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The young lad screams while his skull is forcefully gripped, a large thumb digging into his face as his parent's mighty palm grasps him by the neck. This scene from Abraham's Sacrifice visits the Uffizi Gallery, evoking unease through the artist's chilling rendition of the tormented youth from the scriptural narrative. It seems as if Abraham, instructed by God to kill his son, could break his neck with a single turn. However Abraham's preferred approach involves the metallic steel blade he grips in his remaining hand, prepared to cut Isaac's neck. One certain aspect stands out – whoever modeled as Isaac for this astonishing work demonstrated remarkable acting skill. Within exists not just fear, shock and begging in his darkened eyes but additionally deep grief that a protector could abandon him so utterly.

He adopted a well-known scriptural tale and transformed it so vibrant and raw that its horrors seemed to happen right in view of the viewer

Viewing in front of the artwork, observers identify this as a actual face, an precise depiction of a young subject, because the same boy – identifiable by his tousled locks and almost dark pupils – appears in two other works by Caravaggio. In every instance, that richly expressive visage commands the scene. In Youth With a Ram, he peers playfully from the shadows while embracing a lamb. In Victorious Cupid, he grins with a toughness learned on Rome's alleys, his black plumed wings sinister, a naked adolescent creating chaos in a affluent residence.

Amor Vincit Omnia, presently displayed at a British gallery, constitutes one of the most discomfiting masterpieces ever created. Viewers feel totally unsettled looking at it. Cupid, whose arrows fill people with frequently painful desire, is shown as a very real, brightly illuminated nude figure, standing over overturned objects that comprise stringed instruments, a music score, plate armour and an builder's T-square. This pile of possessions resembles, deliberately, the mathematical and architectural equipment strewn across the ground in Albrecht Dürer's print Melencolia I – except in this case, the melancholic mess is created by this smirking deity and the mayhem he can release.

"Love sees not with the vision, but with the soul, / And thus is winged Cupid depicted blind," wrote the Bard, shortly prior to this work was produced around 1601. But the painter's Cupid is not blind. He gazes straight at the observer. That face – sardonic and ruddy-cheeked, staring with brazen 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 images of the same unusual-appearing kid in the Eternal City at the dawn of the seventeenth century, he was the highly acclaimed sacred artist in a metropolis enflamed by Catholic revival. The Sacrifice of Isaac reveals why he was commissioned to decorate sanctuaries: he could adopt a biblical story that had been portrayed many times previously and render it so fresh, so raw and visceral that the horror seemed to be happening directly in front of the spectator.

Yet there existed a different aspect to the artist, apparent as quickly as he came in Rome in the winter that concluded the sixteenth century, as a artist in his early 20s with no mentor or patron in the city, just skill and boldness. The majority of the paintings with which he captured the holy city's eye were everything but devout. That could be the very first resides in London's art museum. A young man parts his red mouth in a scream of pain: while reaching out his filthy digits for a cherry, he has instead been attacked. Youth Bitten by a Reptile is eroticism amid poverty: viewers can discern Caravaggio's gloomy room reflected in the murky liquid of the glass container.

The boy sports a rose-colored blossom in his coiffure – a symbol of the sex trade in early modern painting. Venetian painters such as Tiziano and Palma Vecchio portrayed prostitutes grasping flowers and, in a painting destroyed in the WWII but known through photographs, Caravaggio portrayed a renowned woman courtesan, clutching a bouquet to her chest. The message of all these floral indicators is clear: sex for sale.

What are we to make of Caravaggio's erotic portrayals of boys – and of a particular adolescent in specific? It is a question that has split his commentators since he gained mega-fame in the twentieth century. The complex historical reality is that the painter was neither the homosexual hero that, for example, the filmmaker presented on screen in his 1986 film Caravaggio, nor so completely pious that, as certain art scholars unbelievably claim, his Boy With a Basket of Fruit is in fact a portrait of Christ.

His early works do offer overt sexual implications, or even offers. It's as if the painter, then a penniless youthful artist, aligned with Rome's sex workers, offering himself to live. In the Florentine gallery, with this idea in mind, viewers might look to an additional early creation, the 1596 masterpiece Bacchus, in which the god of alcohol stares coolly at the spectator as he begins to untie the dark ribbon of his robe.

A few years following Bacchus, what could have motivated Caravaggio to create Amor Vincit Omnia for the artistic patron Vincenzo Giustiniani, when he was finally becoming almost respectable with prestigious church commissions? This profane non-Christian deity revives the erotic provocations of his early works but in a increasingly intense, uneasy way. Half a century later, its secret seemed clear: it was a portrait of the painter's companion. A English traveller saw Victorious Cupid in about 1649 and was told its figure has "the physique and countenance of [Caravaggio's|his] own boy or servant that slept with him". The identity of this adolescent was Cecco.

The painter had been deceased for about 40 years when this account was recorded.