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The young lad cries out as his skull is forcefully gripped, a large thumb digging into his face as his father's mighty palm holds him by the throat. That moment from The Sacrifice of Isaac appears in the Florentine museum, creating distress through Caravaggio's harrowing portrayal of the suffering youth from the scriptural account. The painting seems as if the patriarch, commanded by God to sacrifice his offspring, could break his spinal column with a single twist. However the father's chosen method involves the silvery steel blade he grips in his remaining hand, ready to slit the boy's throat. A definite aspect stands out – whoever posed as the sacrifice for this astonishing work displayed extraordinary acting ability. Within exists not just dread, shock and begging in his shadowed gaze but additionally profound grief that a protector could abandon him so utterly.

The artist took a familiar biblical tale and made it so vibrant and visceral that its horrors seemed to happen directly in front of the viewer

Standing before the painting, observers recognize this as a real face, an accurate record of a adolescent subject, because the identical youth – identifiable by his disheveled hair and nearly dark pupils – appears in two other paintings by the master. In each case, that highly emotional visage dominates the scene. In Youth With a Ram, he gazes mischievously from the darkness while embracing a lamb. In Amor Vincit Omnia, he grins with a hardness acquired on the city's streets, his dark feathery appendages sinister, a naked adolescent creating riot in a affluent dwelling.

Amor Vincit Omnia, presently displayed at a London gallery, represents one of the most discomfiting masterpieces ever created. Observers feel totally unsettled gazing at it. Cupid, whose darts inspire people with frequently painful longing, is portrayed as a very real, vividly illuminated unclothed figure, standing over overturned objects that comprise stringed instruments, a music score, metal armour and an architect's ruler. This pile of possessions resembles, deliberately, the mathematical and architectural equipment strewn across the ground in Albrecht Dürer's engraving Melencolia I – except in this case, the melancholic mess is created by this smirking deity and the turmoil he can release.

"Love looks not with the eyes, but with the mind, / And therefore is winged Cupid painted sightless," wrote Shakespeare, shortly before this painting was produced around the early 1600s. But Caravaggio's Cupid is not blind. He gazes straight at the observer. That face – sardonic and rosy-cheeked, looking with bold confidence as he struts naked – is the same one that shrieks in terror in The Sacrifice of Isaac.

When the Italian master painted his three images of the identical distinctive-appearing youth in the Eternal City at the start of the seventeenth century, he was the most celebrated sacred artist in a city enflamed by religious revival. The Sacrifice of Isaac demonstrates why he was commissioned to decorate sanctuaries: he could take a biblical story that had been depicted many occasions previously and render it so fresh, so raw and physical that the horror seemed to be happening directly before the spectator.

Yet there existed a different aspect to the artist, evident as quickly as he arrived in Rome in the winter that concluded 1592, as a painter in his initial twenties with no teacher or supporter in the urban center, just skill and audacity. Most of the works with which he caught the sacred city's eye were everything but devout. What could be the absolute first hangs in the UK's National Gallery. A young man parts his crimson mouth in a scream of agony: while stretching out his dirty fingers for a fruit, he has rather been bitten. Boy Bitten By a Lizard is sensuality amid poverty: viewers can discern Caravaggio's dismal chamber reflected in the murky waters of the transparent vase.

The adolescent wears a rose-colored flower in his coiffure – a emblem of the sex trade in early modern art. Northern Italian painters such as Titian and Palma Vecchio portrayed prostitutes holding blooms and, in a work destroyed in the WWII but documented through images, Caravaggio represented a famous woman courtesan, holding a bouquet to her chest. The meaning of all these botanical indicators is obvious: sex for purchase.

What are we to make of the artist's erotic depictions of youths – and of one boy in particular? It is a question that has divided his interpreters ever since he achieved widespread recognition in the twentieth century. The complicated past truth is that the painter was not the homosexual icon that, for instance, Derek Jarman presented on film in his twentieth-century movie about the artist, nor so completely pious that, as certain artistic historians improbably assert, his Youth Holding Fruit is in fact a likeness of Jesus.

His early works indeed offer overt sexual implications, or even propositions. It's as if Caravaggio, then a destitute youthful creator, aligned with the city's sex workers, selling himself to survive. In the Uffizi, with this thought in consideration, viewers might turn to another initial creation, the sixteenth-century masterpiece Bacchus, in which the god of alcohol stares calmly at you as he begins to undo the dark ribbon of his garment.

A several years after the wine deity, what could have motivated the artist to create Victorious Cupid for the artistic collector the nobleman, when he was at last growing almost established with important church commissions? This unholy pagan god revives the erotic provocations of his early works but in a increasingly powerful, unsettling manner. Fifty years later, its hidden meaning seemed obvious: it was a portrait of the painter's companion. A English visitor viewed the painting in about 1649 and was informed its subject has "the physique and countenance of [Caravaggio's|his] owne boy or servant that slept with him". The identity of this boy was Cecco.

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