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The young boy screams while his head is forcefully held, a massive thumb pressing into his cheek as his father's mighty hand holds him by the throat. That scene from The Sacrifice of Isaac visits the Uffizi Gallery, creating distress through the artist's harrowing portrayal of the suffering youth from the scriptural account. It appears as if Abraham, instructed by the Divine to sacrifice his offspring, could break his neck with a solitary twist. However Abraham's preferred approach involves the metallic grey blade he holds in his other palm, ready to cut Isaac's neck. One certain element stands out – whomever modeled as the sacrifice for this breathtaking piece displayed remarkable expressive skill. Within exists not only fear, shock and begging in his shadowed eyes but also profound sorrow that a guardian could abandon him so utterly.

The artist took a familiar scriptural tale and made it so fresh and visceral that its horrors appeared to unfold directly in view of the viewer

Viewing in front of the artwork, observers recognize this as a real face, an precise record of a young subject, because the identical youth – recognizable by his tousled hair and almost dark eyes – appears in two other works by the master. In every instance, that highly emotional face commands the scene. In John the Baptist, he gazes mischievously from the shadows while embracing a ram. In Victorious Cupid, he smirks with a hardness learned on the city's alleys, his dark feathery wings sinister, a unclothed child running riot in a affluent dwelling.

Victorious Cupid, presently exhibited at a British gallery, constitutes one of the most embarrassing artworks ever created. Observers feel totally disoriented looking at it. Cupid, whose darts inspire people with frequently painful desire, is shown as a extremely tangible, brightly lit unclothed form, straddling overturned items that comprise stringed devices, a music score, metal armour and an builder's T-square. This pile of possessions resembles, deliberately, the geometric and construction equipment scattered across the floor in Albrecht Dürer's engraving Melencolia I – save here, the melancholic mess is caused by this grinning deity and the mayhem he can release.

"Love looks not with the eyes, but with the soul, / And thus is winged Love depicted blind," wrote Shakespeare, just prior to this painting was produced around 1601. But the painter's Cupid is not blind. He stares directly at you. That countenance – ironic and ruddy-faced, looking with brazen confidence as he struts unclothed – is the same one that shrieks in terror in Abraham's Test.

When Michelangelo Merisi da Caravaggio created his multiple images of the same distinctive-appearing youth in Rome at the dawn of the seventeenth century, he was the most celebrated sacred artist in a metropolis ignited by Catholic renewal. Abraham's Offering reveals why he was sought to decorate churches: he could take a biblical story that had been portrayed numerous occasions before and make it so new, so unfiltered and visceral that the terror seemed to be happening immediately before the spectator.

However there existed a different side to the artist, evident as quickly as he came in Rome in the cold season that ended the sixteenth century, as a artist in his early twenties with no teacher or patron in the city, only skill and boldness. The majority of the paintings with which he caught the sacred city's attention were everything but devout. That may be the very first resides in the UK's art museum. A youth opens his red mouth in a yell of pain: while stretching out his dirty digits for a fruit, he has instead been attacked. Youth Bitten by a Reptile is eroticism amid squalor: observers can see the painter's dismal chamber reflected in the murky liquid of the glass vase.

The boy sports a rose-colored flower in his hair – a emblem of the erotic trade in early modern painting. Northern Italian artists such as Titian and Palma Vecchio depicted courtesans grasping blooms and, in a painting lost in the WWII but known through images, Caravaggio represented a renowned woman courtesan, clutching a bouquet to her bosom. The message of all these botanical indicators is clear: intimacy for purchase.

What are we to interpret of Caravaggio's sensual depictions of boys – and of a particular adolescent in specific? It is a inquiry that has split his commentators since he achieved mega-fame in the twentieth century. The complex historical reality is that the artist was neither the homosexual hero that, for instance, Derek Jarman presented on screen in his twentieth-century movie Caravaggio, nor so completely devout that, as some art scholars improbably claim, his Youth Holding Fruit is actually a likeness of Christ.

His early works do make overt erotic suggestions, or including propositions. It's as if Caravaggio, then a penniless young artist, aligned with the city's prostitutes, selling himself to live. In the Uffizi, with this thought in consideration, viewers might look to an additional initial work, the 1596 masterpiece Bacchus, in which the god of wine stares calmly at you as he begins to untie the black ribbon of his garment.

A few annums following Bacchus, what could have driven the artist to paint Amor Vincit Omnia for the artistic patron Vincenzo Giustiniani, when he was finally becoming nearly respectable with important church projects? This unholy pagan deity revives the erotic provocations of his early paintings but in a more powerful, unsettling way. Half a century afterwards, its hidden meaning seemed clear: it was a representation of Caravaggio's companion. A British visitor viewed Victorious Cupid in about the mid-seventeenth century and was informed its figure has "the body & face of [Caravaggio's|his] owne youth or assistant that laid with him". The name of this adolescent was Francesco.

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