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The young lad screams while his head is firmly gripped, a large thumb digging into his face as his father's mighty palm grasps him by the throat. That moment from Abraham's Sacrifice appears in the Uffizi Gallery, evoking distress through Caravaggio's harrowing rendition of the suffering child from the biblical narrative. The painting seems as if the patriarch, commanded by God to sacrifice his son, could break his spinal column with a solitary twist. Yet Abraham's chosen approach involves the silvery steel knife he grips in his other hand, prepared to cut the boy's neck. One definite element remains – whomever modeled as Isaac for this breathtaking work demonstrated extraordinary expressive skill. There exists not only fear, shock and pleading in his darkened gaze but additionally deep sorrow that a guardian could abandon him so utterly.

The artist took a familiar scriptural story and transformed it so vibrant and visceral that its horrors appeared to happen directly in view of you

Viewing before the artwork, observers identify this as a real countenance, an accurate depiction of a adolescent model, because the same boy – recognizable by his tousled hair and nearly black eyes – appears in two other paintings by the master. In each case, that highly emotional face dominates the composition. In Youth With a Ram, he peers mischievously from the darkness while holding a ram. In Victorious Cupid, he smirks with a hardness learned on Rome's streets, his black feathery appendages demonic, a unclothed child creating riot in a well-to-do dwelling.

Victorious Cupid, presently exhibited at a London museum, represents one of the most embarrassing artworks ever painted. Viewers feel completely unsettled gazing at it. Cupid, whose darts fill people with often agonizing longing, is portrayed as a extremely real, brightly lit unclothed figure, standing over overturned objects that include musical devices, a musical manuscript, metal armor and an builder's ruler. This pile of possessions resembles, intentionally, the mathematical and architectural equipment strewn across the ground in the German master's engraving Melencolia I – save in this case, the melancholic mess is caused by this grinning deity and the turmoil he can release.

"Love sees not with the vision, but with the soul, / And therefore is feathered Cupid painted blind," penned Shakespeare, shortly prior to this work was produced around 1601. But the painter's Cupid is not unseeing. He stares straight at you. That countenance – sardonic and rosy-cheeked, looking with bold assurance as he poses unclothed – is the identical one that screams in fear in Abraham's Test.

When Michelangelo Merisi da Caravaggio created his multiple portrayals of the identical unusual-looking kid in Rome at the start of the seventeenth century, he was the most acclaimed sacred artist in a city enflamed by religious revival. Abraham's Offering demonstrates why he was commissioned to adorn sanctuaries: he could adopt a scriptural story that had been portrayed many times previously and make it so fresh, so raw and physical that the terror seemed to be occurring immediately in front of the spectator.

Yet there existed another aspect to the artist, evident as soon as he came in the capital in the winter that concluded the sixteenth century, as a painter in his initial 20s with no teacher or patron in the city, just talent and audacity. The majority of the paintings with which he captured the holy metropolis's attention were anything but devout. That could be the very first hangs in the UK's art museum. A young man parts his red lips in a scream of pain: while stretching out his dirty digits for a fruit, he has instead been attacked. Boy Bitten By a Lizard is sensuality amid poverty: observers can see Caravaggio's gloomy chamber mirrored in the cloudy liquid of the transparent container.

The boy sports a pink flower in his hair – a emblem of the sex commerce in early modern painting. Venetian artists such as Titian and Palma Vecchio depicted prostitutes holding blooms and, in a painting lost in the second world war but documented through photographs, Caravaggio represented a renowned female courtesan, clutching a bouquet to her chest. The message of all these floral indicators is obvious: sex for sale.

What are we to make of Caravaggio's erotic portrayals of boys – and of a particular boy in specific? It is a question that has split his interpreters ever since he gained mega-fame in the twentieth century. The complicated past truth is that the painter was not the queer hero that, for instance, Derek Jarman presented on film in his 1986 film Caravaggio, nor so completely devout that, as some artistic historians unbelievably assert, his Youth Holding Fruit is actually a likeness of Jesus.

His initial paintings do offer explicit erotic suggestions, or even propositions. It's as if Caravaggio, then a penniless young artist, aligned with the city's prostitutes, selling himself to survive. In the Uffizi, with this thought in mind, observers might turn to another early creation, the 1596 masterwork the god of wine, in which the god of alcohol gazes coolly at you as he begins to undo the black ribbon of his garment.

A few years following Bacchus, what could have motivated Caravaggio to paint Amor Vincit Omnia for the artistic patron the nobleman, when he was at last becoming nearly respectable with important church projects? This profane pagan god revives the erotic challenges of his early paintings but in a increasingly powerful, unsettling way. Half a century afterwards, its secret seemed clear: it was a representation of Caravaggio's lover. A British traveller viewed Victorious Cupid in about 1649 and was told its figure has "the body & face of [Caravaggio's|his] owne youth or assistant that slept with him". The name of this adolescent was Cecco.

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