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A youthful lad cries out while his head is firmly held, a massive thumb pressing into his cheek as his father's mighty palm grasps him by the throat. This moment from Abraham's Sacrifice visits the Uffizi Gallery, creating unease through the artist's chilling portrayal of the tormented child from the biblical narrative. The painting seems as if the patriarch, commanded by God to sacrifice his offspring, could break his neck with a solitary twist. However Abraham's chosen method involves the silvery steel knife he grips in his remaining palm, prepared to cut Isaac's neck. One certain element remains – whomever modeled as Isaac for this breathtaking work demonstrated remarkable acting skill. Within exists not only dread, surprise and begging in his darkened eyes but additionally deep sorrow that a protector could abandon him so completely.

He adopted a well-known biblical story and made it so vibrant and raw that its horrors appeared to happen directly in view of the viewer

Standing in front of the painting, viewers recognize this as a real countenance, an accurate depiction of a young subject, because the same boy – identifiable by his tousled locks and nearly black eyes – appears in several additional works by Caravaggio. In each instance, that richly expressive face dominates the scene. In John the Baptist, he peers playfully from the darkness while holding a ram. In Amor Vincit Omnia, he smirks with a toughness learned on the city's alleys, his black plumed wings demonic, a naked adolescent running riot in a affluent residence.

Amor Vincit Omnia, currently displayed at a British museum, constitutes one of the most discomfiting artworks ever painted. Observers feel completely disoriented gazing at it. Cupid, whose darts fill people with often agonizing longing, is shown as a extremely real, brightly lit nude form, straddling toppled-over objects that include musical instruments, a music score, plate armor and an builder's T-square. This pile of possessions resembles, deliberately, the mathematical and architectural equipment strewn across the ground in the German master's print Melancholy – except 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 soul, / And therefore is feathered Cupid painted sightless," wrote Shakespeare, shortly before this painting was produced around the early 1600s. But Caravaggio's Cupid is not blind. He stares straight at the observer. That countenance – sardonic and rosy-cheeked, staring with brazen assurance as he poses naked – is the identical one that screams in terror in Abraham's Test.

As the Italian master painted his multiple images of the same unusual-appearing youth in Rome at the start of the 17th century, he was the highly acclaimed religious painter in a metropolis ignited by Catholic revival. Abraham's Offering reveals why he was sought to decorate sanctuaries: he could take a scriptural narrative that had been portrayed many occasions previously and make it so fresh, so unfiltered and visceral that the terror appeared to be occurring directly before the spectator.

Yet there was another side to the artist, apparent as quickly as he came in the capital in the cold season that concluded the sixteenth century, as a painter in his early twenties with no teacher or patron in the city, only skill and audacity. Most of the paintings with which he caught the sacred metropolis's eye were anything but devout. What may be the very first resides in London's National Gallery. A youth parts his red lips in a scream of agony: while reaching out his dirty digits for a fruit, he has instead been attacked. Youth Bitten by a Reptile is sensuality amid poverty: viewers can discern the painter's gloomy chamber mirrored in the murky liquid of the transparent vase.

The boy wears a pink blossom in his hair – a symbol of the erotic commerce in Renaissance art. Northern Italian painters such as Titian and Palma Vecchio portrayed courtesans grasping flowers and, in a painting lost in the second world war but documented through images, the master portrayed a famous female courtesan, holding a bouquet to her chest. The meaning of all these botanical signifiers is obvious: sex for sale.

What are we to interpret of Caravaggio's erotic portrayals of boys – and of a particular boy in specific? It is a question that has split his interpreters since he achieved widespread recognition in the twentieth century. The complex past reality is that the painter was not the queer icon that, for example, the filmmaker presented on screen in his twentieth-century movie Caravaggio, nor so entirely devout that, as certain art historians unbelievably claim, his Boy With a Basket of Fruit is in fact a likeness of Christ.

His early works do make overt sexual implications, or including offers. It's as if Caravaggio, then a penniless young creator, aligned with Rome's prostitutes, offering himself to live. In the Florentine gallery, with this idea in consideration, viewers might look to an additional initial work, the sixteenth-century masterpiece the god of wine, in which the deity of wine gazes calmly at the spectator as he starts to undo the dark ribbon of his robe.

A few years after Bacchus, what could have driven Caravaggio to create Amor Vincit Omnia for the art patron Vincenzo Giustiniani, when he was finally becoming nearly respectable with prestigious ecclesiastical projects? This profane pagan god revives the sexual provocations of his initial paintings but in a increasingly powerful, unsettling manner. Fifty years later, its secret seemed clear: it was a portrait of the painter's companion. A English traveller viewed Victorious Cupid in about 1649 and was informed its subject has "the body & face of [Caravaggio's|his] own youth or servant that slept with him". The name of this boy was Cecco.

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