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A young boy cries out while his skull is firmly held, a large thumb pressing into his cheek as his father's powerful palm grasps him by the throat. That scene from The Sacrifice of Isaac visits the Uffizi Gallery, evoking unease through Caravaggio's chilling rendition of the tormented youth from the scriptural narrative. It appears as if the patriarch, instructed by God to kill his son, could snap his neck with a single twist. However Abraham's preferred method involves the metallic grey blade he grips in his other hand, ready to cut the boy's neck. A certain element remains – whomever posed as the sacrifice for this breathtaking work displayed remarkable acting skill. There exists not only fear, surprise and begging in his darkened gaze but also deep grief that a protector could betray him so utterly.

The artist adopted a familiar scriptural story and transformed it so fresh and visceral that its horrors seemed to happen directly in front of you

Standing before the artwork, observers recognize this as a actual face, an precise record of a adolescent model, because the identical youth – identifiable by his disheveled locks and nearly black pupils – appears in two additional paintings by Caravaggio. In every instance, that highly emotional face commands the composition. In Youth With a Ram, he peers mischievously from the shadows while embracing a lamb. In Victorious Cupid, he smirks with a hardness learned on the city's streets, his black feathery appendages demonic, a unclothed child running riot in a affluent residence.

Victorious Cupid, presently exhibited at a London gallery, represents one of the most embarrassing masterpieces ever painted. Observers feel totally unsettled gazing at it. Cupid, whose darts inspire people with often agonizing desire, is portrayed as a extremely tangible, vividly lit unclothed form, straddling overturned objects that include musical devices, a musical manuscript, plate armor and an builder's ruler. This pile of possessions resembles, intentionally, the geometric and architectural equipment scattered across the floor in Albrecht Dürer's print Melancholy – save here, the melancholic disorder is caused by this smirking Cupid and the mayhem he can release.

"Love sees not with the eyes, but with the mind, / And therefore is feathered Love painted sightless," penned the Bard, just before this painting was produced around 1601. But the painter's god is not blind. He gazes directly at the observer. That countenance – sardonic and ruddy-cheeked, looking with bold assurance as he struts naked – is the same one that screams in terror in The Sacrifice of Isaac.

When Michelangelo Merisi da Caravaggio created his three portrayals of the identical unusual-appearing youth in the Eternal City at the start of the 17th century, he was the most acclaimed religious painter in a city ignited by religious renewal. Abraham's Offering reveals why he was sought to decorate churches: he could take a biblical story that had been depicted many occasions previously and make it so new, so raw and physical that the horror seemed to be occurring directly before the spectator.

Yet there existed another aspect to Caravaggio, evident as quickly as he arrived in Rome in the winter that ended the sixteenth century, as a painter in his initial 20s with no teacher or supporter in the urban center, just talent and audacity. Most of the paintings with which he captured the sacred metropolis's attention were anything but devout. What could be the very first resides in the UK's art museum. A youth opens his crimson mouth in a scream of agony: while stretching out his dirty fingers for a cherry, he has rather been bitten. Youth Bitten by a Reptile is eroticism amid squalor: observers can see the painter's gloomy chamber mirrored in the murky liquid of the transparent vase.

The boy sports a pink blossom in his hair – a emblem of the erotic commerce in early modern painting. Northern Italian painters such as Tiziano and Jacopo Palma depicted courtesans holding flowers and, in a work destroyed in the WWII but documented through photographs, Caravaggio represented a famous woman courtesan, clutching a bouquet to her bosom. The message of all these botanical indicators is obvious: sex for sale.

What are we to make of the artist's erotic depictions of youths – and of one boy in particular? It is a inquiry that has divided his interpreters since he achieved widespread recognition in the 1980s. The complex historical truth is that the painter was neither the homosexual hero that, for instance, Derek Jarman put on film in his twentieth-century movie Caravaggio, nor so entirely pious that, as certain art scholars improbably 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 artist, aligned with the city's sex workers, selling himself to live. In the Florentine gallery, with this thought in mind, observers might turn to an additional early work, the sixteenth-century masterwork the god of wine, in which the deity of wine gazes calmly at the spectator as he starts to undo the dark sash of his robe.

A several years after Bacchus, what could have driven the artist to create Victorious Cupid for the artistic patron Vincenzo Giustiniani, when he was finally growing nearly respectable with important ecclesiastical projects? This unholy non-Christian deity resurrects the sexual challenges of his initial works but in a more intense, unsettling way. Half a century later, its secret seemed clear: it was a portrait of the painter's lover. A English traveller saw 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 servant that slept with him". The name of this boy was Cecco.

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