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The young lad screams as his skull is firmly gripped, a large digit pressing into his face as his parent's powerful palm holds him by the neck. This scene from The Sacrifice of Isaac appears in the Florentine museum, creating unease through Caravaggio's chilling portrayal of the tormented child from the biblical account. The painting appears as if the patriarch, instructed by the Divine to sacrifice his offspring, could break his spinal column with a solitary twist. Yet the father's chosen method involves the silvery grey blade he holds in his remaining palm, ready to cut the boy's neck. One certain element stands out – whoever modeled as Isaac for this breathtaking piece displayed remarkable expressive ability. There exists not just dread, shock and begging in his shadowed gaze but additionally profound sorrow that a guardian could betray him so completely.

The artist adopted a familiar biblical story and made it so fresh and raw that its terrors appeared to happen right in front of the viewer

Viewing before the painting, observers identify this as a actual countenance, an accurate depiction of a adolescent model, because the same youth – recognizable by his tousled hair and nearly black eyes – appears in two additional paintings by the master. In every instance, that highly expressive visage dominates the composition. In John the Baptist, he peers playfully from the shadows while embracing a ram. In Amor Vincit Omnia, he grins with a hardness learned on Rome's alleys, his dark feathery wings demonic, a unclothed adolescent creating chaos in a affluent dwelling.

Amor Vincit Omnia, currently displayed at a London museum, represents one of the most discomfiting masterpieces ever created. Observers feel completely unsettled gazing at it. The god of love, whose arrows inspire people with frequently agonizing longing, is portrayed as a very tangible, vividly lit nude figure, standing over toppled-over objects that include stringed devices, a musical score, plate armour and an architect's T-square. This heap of possessions echoes, intentionally, the geometric and construction gear scattered across the ground in the German master's print Melencolia I – save in this case, the melancholic mess is caused by this grinning Cupid and the mayhem he can release.

"Love sees not with the vision, but with the soul, / And thus is winged Love depicted blind," wrote Shakespeare, shortly before this painting was created around 1601. But the painter's Cupid is not blind. He stares straight at the observer. That countenance – sardonic and rosy-faced, looking with brazen assurance as he poses naked – is the same one that screams in fear in The Sacrifice of Isaac.

When the Italian master painted his three images of the same unusual-looking kid in Rome at the dawn of the seventeenth century, he was the most acclaimed religious painter in a metropolis enflamed by religious renewal. The Sacrifice of Isaac reveals why he was sought to decorate sanctuaries: he could take a biblical story that had been depicted numerous occasions previously and make it so fresh, so unfiltered and physical that the horror seemed to be happening directly in front of the spectator.

However there existed another aspect to Caravaggio, apparent as quickly as he arrived in the capital in the winter that concluded the sixteenth century, as a painter in his early twenties with no teacher or patron in the urban center, only skill and audacity. Most of the works with which he captured the holy metropolis's attention were anything but holy. What may be the absolute first hangs in London's art museum. A youth parts his crimson lips in a yell of agony: while reaching out his dirty digits for a cherry, he has rather been bitten. Youth Bitten by a Reptile is sensuality amid squalor: viewers can see Caravaggio's dismal chamber reflected in the cloudy waters of the transparent container.

The boy sports a rose-colored flower in his hair – a emblem of the erotic trade in Renaissance art. Venetian painters such as Tiziano and Palma Vecchio depicted prostitutes holding blooms and, in a work destroyed in the WWII but known through photographs, the master portrayed a famous female prostitute, clutching a posy to her chest. The message of all these floral indicators is obvious: sex for sale.

What are we to make of Caravaggio's sensual portrayals of youths – and of a particular adolescent in particular? It is a inquiry that has divided his commentators since he gained widespread recognition in the twentieth century. The complicated past reality is that the artist was not the queer icon that, for instance, Derek Jarman presented on film in his twentieth-century movie about the artist, nor so entirely pious that, as certain art historians improbably assert, his Youth Holding Fruit is in fact a portrait of Christ.

His early works do offer overt sexual implications, or even offers. It's as if Caravaggio, then a penniless youthful artist, aligned with the city's prostitutes, offering himself to survive. In the Florentine gallery, with this idea in consideration, observers might look to an additional initial work, the sixteenth-century masterpiece Bacchus, in which the deity of alcohol stares calmly at the spectator as he begins to untie the black ribbon of his garment.

A few years following Bacchus, what could have driven Caravaggio to paint Victorious Cupid for the artistic patron Vincenzo Giustiniani, when he was at last growing nearly established with prestigious ecclesiastical commissions? This profane non-Christian god resurrects the sexual challenges of his initial paintings but in a more powerful, uneasy manner. Fifty years afterwards, its hidden meaning seemed clear: it was a portrait of Caravaggio's lover. A British traveller saw Victorious Cupid in about the mid-seventeenth century and was told its subject has "the body & face of [Caravaggio's|his] own boy or assistant that slept with him". The identity of this boy was Cecco.

The artist had been dead for about forty years when this account was documented.