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The youthful lad cries out as his head is firmly held, a massive thumb pressing into his cheek as his father's powerful hand grasps him by the neck. This scene from The Sacrifice of Isaac appears in the Florentine museum, creating distress through Caravaggio's harrowing rendition of the suffering youth from the biblical account. It seems as if Abraham, instructed by God to kill his offspring, could break his spinal column with a single turn. However Abraham's preferred approach involves the silvery steel knife he holds in his other palm, prepared to slit the boy's neck. One definite aspect remains – whomever posed as the sacrifice for this astonishing piece demonstrated extraordinary acting ability. There exists not just dread, surprise and pleading in his darkened gaze but also deep grief that a protector could betray him so completely.

The artist took a well-known biblical story and transformed it so fresh and visceral that its horrors appeared to unfold right in front of you

Viewing before the painting, viewers recognize this as a real face, an accurate depiction of a young subject, because the same youth – identifiable by his tousled locks and almost black pupils – features in two other paintings by Caravaggio. In every instance, that richly expressive visage dominates the scene. In Youth With a Ram, he peers mischievously from the shadows while embracing a ram. In Amor Vincit Omnia, he smirks with a toughness acquired on the city's streets, his dark plumed wings demonic, a naked child creating chaos in a affluent dwelling.

Victorious Cupid, currently displayed at a London museum, constitutes one of the most discomfiting masterpieces ever created. Observers feel completely disoriented looking at it. The god of love, whose arrows inspire people with frequently painful desire, is portrayed as a very tangible, vividly illuminated nude form, standing over toppled-over items that include stringed instruments, a music manuscript, metal armour and an builder's T-square. This pile of items echoes, deliberately, the geometric and construction equipment strewn across the ground in the German master's print Melencolia I – except here, the melancholic mess is caused by this smirking deity and the turmoil he can unleash.

"Affection looks not with the eyes, but with the mind, / And therefore is feathered Cupid painted sightless," wrote the Bard, shortly before this work was created around 1601. But the painter's god is not blind. He gazes straight at you. That countenance – ironic and rosy-cheeked, staring with bold assurance as he struts unclothed – is the same one that shrieks in terror in Abraham's Test.

As Michelangelo Merisi da Caravaggio painted his multiple images of the same distinctive-appearing kid in the Eternal City at the start of the 17th century, he was the most celebrated sacred artist in a city ignited by Catholic renewal. The Sacrifice of Isaac demonstrates why he was commissioned to adorn sanctuaries: he could adopt a biblical narrative that had been portrayed many times before and make it so new, so raw and visceral that the terror appeared to be happening directly before the spectator.

However there was a different side to Caravaggio, apparent as quickly as he came in the capital in the cold season that ended 1592, as a artist in his early 20s with no mentor or patron in the urban center, just talent and audacity. Most of the works with which he captured the holy metropolis's eye were everything but holy. That could be the absolute first resides in London's art museum. A young man parts his red mouth in a yell of agony: while stretching out his filthy digits for a cherry, he has instead been bitten. Youth Bitten by a Reptile is sensuality amid poverty: observers can discern the painter's dismal room reflected in the murky liquid of the glass vase.

The adolescent sports a rose-colored flower in his hair – a emblem of the sex trade in Renaissance art. Northern Italian painters such as Tiziano and Jacopo Palma depicted courtesans grasping blooms and, in a work destroyed in the second world war but documented through photographs, the master portrayed a famous female prostitute, holding a posy to her bosom. The meaning of all these floral indicators is obvious: intimacy for sale.

What are we to interpret of Caravaggio's erotic depictions of boys – and of one boy in particular? It is a question that has split his interpreters since he gained mega-fame in the twentieth century. The complex past reality is that the artist was neither the queer hero that, for instance, the filmmaker presented on film in his twentieth-century movie Caravaggio, nor so completely devout that, as certain artistic scholars unbelievably claim, his Boy With a Basket of Fruit is in fact a portrait of Jesus.

His initial works indeed offer explicit erotic implications, or even propositions. It's as if Caravaggio, then a penniless young creator, identified with Rome's prostitutes, offering himself to live. In the Florentine gallery, with this thought in consideration, viewers might turn to an additional initial work, the 1596 masterwork Bacchus, in which the god of alcohol stares calmly at the spectator as he starts to untie the dark ribbon of his garment.

A few annums after the wine deity, what could have motivated the artist to create Amor Vincit Omnia for the artistic collector the nobleman, when he was at last becoming nearly established with prestigious church commissions? This profane pagan god revives the erotic provocations of his initial works but in a increasingly intense, unsettling way. Half a century afterwards, its hidden meaning seemed clear: it was a portrait of Caravaggio's lover. A English traveller viewed Victorious Cupid in about 1649 and was told its figure has "the body & face of [Caravaggio's|his] owne youth or servant that slept with him". The name of this boy was Cecco.

The painter had been deceased for about 40 annums when this story was documented.