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The young lad screams while his head is forcefully held, a large digit digging into his face as his father's powerful palm holds him by the throat. This moment from The Sacrifice of Isaac visits the Uffizi Gallery, creating unease through the artist's harrowing portrayal of the tormented youth from the scriptural account. The painting seems as if the patriarch, commanded by God to sacrifice his son, could break his spinal column with a single twist. However the father's preferred method involves the metallic grey knife he holds in his remaining hand, prepared to cut the boy's throat. A definite aspect remains – whomever posed as the sacrifice for this astonishing piece displayed extraordinary acting skill. Within exists not only fear, shock and begging in his shadowed gaze but also profound grief that a protector could abandon him so completely.

He adopted a familiar scriptural tale and transformed it so fresh and visceral that its horrors seemed to unfold directly in view of the viewer

Viewing before the painting, observers identify this as a actual countenance, an precise record of a young model, because the identical youth – recognizable by his tousled locks and almost black eyes – appears in several other paintings by Caravaggio. In every case, that richly emotional visage commands the composition. In Youth With a Ram, he peers mischievously from the shadows while embracing a ram. In Victorious Cupid, he grins with a toughness acquired on the city's streets, his black plumed wings demonic, a naked adolescent running riot in a affluent dwelling.

Victorious Cupid, presently displayed at a London gallery, constitutes one of the most discomfiting artworks ever painted. Observers feel totally disoriented gazing at it. Cupid, whose darts fill people with often painful desire, is shown as a extremely tangible, brightly lit nude figure, straddling overturned objects that comprise musical instruments, a music score, metal armor and an architect's ruler. This pile of possessions echoes, intentionally, the mathematical and construction equipment strewn across the ground in the German master's engraving Melencolia I – save here, the gloomy mess is created by this smirking Cupid and the turmoil he can release.

"Love looks not with the eyes, but with the soul, / And thus is feathered Love depicted blind," wrote the Bard, just prior to this painting was produced around 1601. But the painter's god is not unseeing. He stares directly at you. That face – ironic and ruddy-cheeked, looking with brazen assurance as he poses unclothed – is the identical one that shrieks in terror in The Sacrifice of Isaac.

When Michelangelo Merisi da Caravaggio created his multiple portrayals of the same unusual-appearing youth in Rome at the start of the seventeenth century, he was the highly celebrated religious artist in a city enflamed by religious revival. Abraham's Offering demonstrates why he was sought to adorn churches: he could adopt a scriptural narrative that had been depicted many times previously and render it so new, so unfiltered and visceral that the terror appeared to be occurring directly before you.

Yet there existed a different side to the artist, apparent as quickly as he came in the capital in the cold season that ended 1592, as a painter in his early twenties with no teacher or patron in the city, just skill and audacity. Most of the works with which he caught the holy metropolis's attention were anything but devout. That may be the absolute first resides in the UK's art museum. A youth parts his crimson lips in a scream of agony: while reaching out his filthy fingers for a fruit, he has rather been attacked. Boy Bitten By a Lizard is sensuality amid poverty: viewers can see the painter's gloomy chamber mirrored in the murky waters of the glass container.

The boy sports a pink flower in his hair – a symbol of the sex trade in early modern painting. Venetian painters such as Titian and Palma Vecchio depicted prostitutes holding flowers and, in a work lost in the WWII but known through photographs, the master portrayed a famous woman prostitute, clutching a posy to her chest. The message of all these botanical signifiers is clear: intimacy for sale.

How are we to make of Caravaggio's sensual depictions of youths – and of a particular adolescent in specific? It is a question that has divided his interpreters since he achieved widespread recognition in the twentieth century. The complex historical truth is that the painter was not the queer icon that, for example, Derek Jarman put on film in his 1986 movie about the artist, nor so entirely pious that, as some artistic scholars improbably claim, his Youth Holding Fruit is in fact a likeness of Christ.

His initial paintings do offer explicit erotic implications, or even offers. It's as if the painter, then a destitute young artist, aligned with Rome's sex workers, offering himself to survive. In the Florentine gallery, with this thought in mind, viewers might look to another early creation, the 1596 masterpiece the god of wine, in which the deity of wine stares calmly at the spectator as he starts to undo the black ribbon of his robe.

A few years after Bacchus, what could have motivated Caravaggio to create Victorious Cupid for the art patron Vincenzo Giustiniani, when he was finally growing almost established with prestigious ecclesiastical commissions? This profane pagan deity resurrects the erotic challenges of his initial paintings but in a more intense, uneasy way. Half a century later, its hidden meaning seemed obvious: it was a representation of the painter's companion. A British traveller viewed Victorious Cupid in about the mid-seventeenth century and was told its subject has "the physique and countenance of [Caravaggio's|his] own boy or assistant that slept with him". The name of this boy was Francesco.

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