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The youthful lad cries out while his skull is firmly held, a massive digit pressing into his face as his father's mighty palm holds him by the neck. This scene from Abraham's Sacrifice appears in the Florentine museum, creating unease through Caravaggio's chilling portrayal of the tormented child from the biblical narrative. The painting seems as if the patriarch, instructed by the Divine to kill his offspring, could snap his neck with a solitary twist. Yet the father's chosen approach involves the silvery steel knife he grips in his remaining palm, ready to slit the boy's throat. A certain element stands out – whoever modeled as the sacrifice for this breathtaking work displayed extraordinary expressive ability. Within exists not just fear, surprise and pleading in his darkened eyes but additionally profound sorrow that a guardian could betray him so utterly.

He took a well-known biblical story and transformed it so fresh and visceral that its horrors appeared to happen directly in front of you

Viewing before the painting, observers identify this as a real countenance, an precise record of a adolescent subject, because the identical youth – identifiable by his disheveled hair and nearly dark eyes – appears in several other works by the master. In each instance, that richly emotional visage commands the composition. In Youth With a Ram, he gazes playfully from the shadows while embracing a ram. In Amor Vincit Omnia, he smirks with a hardness acquired on Rome's streets, his dark plumed appendages sinister, a naked child running riot in a well-to-do dwelling.

Victorious Cupid, currently exhibited at a British gallery, constitutes one of the most embarrassing masterpieces ever created. Viewers feel totally unsettled gazing at it. Cupid, whose arrows inspire people with often agonizing desire, is portrayed as a very tangible, brightly illuminated nude figure, standing over overturned items that include stringed devices, a music score, plate armour and an architect's T-square. This pile of items echoes, deliberately, the geometric and architectural gear strewn across the ground in the German master's print Melencolia I – save in this case, the gloomy disorder is caused by this grinning deity and the mayhem he can unleash.

"Affection looks not with the vision, but with the mind, / And therefore is winged Love painted sightless," wrote the Bard, shortly before this painting was created around 1601. But Caravaggio's god is not unseeing. He stares directly at the observer. That countenance – sardonic and ruddy-faced, looking with bold assurance as he poses naked – is the identical one that screams in fear in Abraham's Test.

As Michelangelo Merisi da Caravaggio created his multiple portrayals of the identical unusual-looking youth in Rome at the start of the 17th century, he was the highly acclaimed religious painter in a metropolis enflamed by religious revival. Abraham's Offering reveals why he was sought to decorate sanctuaries: he could take a scriptural story that had been portrayed numerous occasions before and render it so fresh, so unfiltered and physical that the horror seemed to be happening immediately in front of you.

Yet there was a different side to the artist, apparent as quickly as he came in the capital in the winter that concluded the sixteenth century, as a painter in his early 20s with no teacher or supporter in the city, only talent and boldness. The majority of the works with which he captured the holy metropolis's eye were anything but devout. That may be the absolute earliest hangs in the UK's National Gallery. A young man opens his crimson mouth in a yell of pain: while stretching out his filthy fingers for a fruit, he has rather been bitten. Boy Bitten By a Lizard is eroticism amid poverty: observers can see the painter's dismal room reflected in the murky waters of the transparent container.

The boy sports a rose-colored blossom in his hair – a symbol of the erotic trade in early modern art. Venetian artists such as Titian and Palma Vecchio portrayed courtesans grasping flowers and, in a painting destroyed in the second world war but documented through images, Caravaggio portrayed a renowned female courtesan, holding a bouquet to her chest. The message of all these botanical signifiers is obvious: sex for purchase.

What are we to make of the artist's erotic portrayals of boys – and of one adolescent in particular? It is a question that has split his interpreters since he achieved mega-fame in the 1980s. The complex historical truth is that the painter was not the homosexual hero that, for instance, the filmmaker presented on screen in his twentieth-century film Caravaggio, nor so entirely pious that, as some artistic historians unbelievably assert, his Boy With a Basket of Fruit is actually a likeness of Christ.

His early paintings indeed make overt sexual suggestions, or even offers. It's as if Caravaggio, then a destitute youthful creator, aligned with Rome's prostitutes, selling himself to survive. In the Uffizi, with this thought in consideration, viewers might turn to another early work, the sixteenth-century masterpiece Bacchus, in which the deity of alcohol stares calmly at you as he begins to undo the dark ribbon of his robe.

A several years after the wine deity, what could have motivated the artist to paint Victorious Cupid for the art collector Vincenzo Giustiniani, when he was finally growing almost established with important church projects? This profane pagan god resurrects the erotic provocations of his early works but in a more intense, uneasy way. Fifty years later, its hidden meaning seemed clear: it was a representation of Caravaggio's companion. A British traveller saw the painting in about 1649 and was informed its subject has "the physique and countenance of [Caravaggio's|his] own boy or servant that slept with him". The name of this boy was Cecco.

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