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A youthful boy cries out while his head is firmly gripped, a large digit pressing into his face as his father's mighty hand holds him by the neck. This scene from Abraham's Sacrifice visits the Florentine museum, evoking unease through the artist's chilling portrayal of the suffering youth from the scriptural account. The painting appears as if Abraham, commanded by God to kill his son, could snap his spinal column with a solitary twist. However Abraham's chosen approach involves the silvery steel blade he holds in his remaining hand, prepared to slit Isaac's throat. A certain aspect stands out – whomever modeled as the sacrifice for this breathtaking work demonstrated extraordinary acting skill. Within exists not only fear, surprise and begging in his shadowed gaze but also profound sorrow that a guardian could abandon him so utterly.

He took a well-known biblical tale and made it so fresh and raw that its terrors appeared to happen directly in front of the viewer

Viewing before the painting, viewers recognize this as a actual countenance, an precise depiction of a adolescent subject, because the same youth – identifiable by his disheveled hair and nearly dark pupils – features in several additional works by Caravaggio. In each instance, that richly expressive visage commands the scene. In John the Baptist, he peers mischievously from the shadows while holding a ram. In Victorious Cupid, he smirks with a hardness learned on Rome's streets, his dark plumed wings sinister, a unclothed child creating chaos in a affluent dwelling.

Amor Vincit Omnia, currently displayed at a London museum, represents one of the most discomfiting artworks ever painted. Observers feel totally disoriented gazing at it. The god of love, whose arrows inspire people with frequently painful longing, is portrayed as a very tangible, vividly lit unclothed figure, straddling overturned items that comprise stringed instruments, a music score, metal armor and an architect'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 here, the melancholic mess is caused by this grinning Cupid and the turmoil he can release.

"Affection sees not with the eyes, but with the soul, / And thus is winged Love painted blind," penned the Bard, shortly before this work was created around 1601. But the painter's Cupid is not blind. He gazes directly at you. That countenance – sardonic and ruddy-faced, staring with brazen assurance as he struts naked – is the same one that screams in terror in Abraham's Test.

As Michelangelo Merisi da Caravaggio painted his three portrayals of the same unusual-appearing kid in Rome at the dawn of the 17th century, he was the most acclaimed sacred artist in a metropolis enflamed by Catholic revival. Abraham's Offering demonstrates why he was commissioned to decorate sanctuaries: he could take a scriptural narrative that had been depicted many occasions before and render it so fresh, so unfiltered and physical that the terror appeared to be occurring directly in front of you.

However there existed another aspect to Caravaggio, apparent as soon as he came in Rome in the winter that concluded the sixteenth century, as a painter in his initial 20s with no mentor or patron in the city, only skill and audacity. The majority of the works with which he captured the holy city's attention were anything but devout. What could be the absolute earliest hangs in London's art museum. A young man opens his crimson lips in a yell of pain: while reaching out his dirty fingers for a fruit, he has instead been attacked. Youth Bitten by a Reptile is eroticism amid squalor: observers can see Caravaggio's dismal room mirrored in the cloudy liquid of the glass vase.

The adolescent wears a rose-colored blossom in his hair – a symbol of the sex trade in early modern art. Northern Italian artists such as Tiziano and Palma Vecchio depicted prostitutes holding blooms and, in a work lost in the WWII but documented through images, Caravaggio portrayed a renowned woman courtesan, holding a posy to her bosom. The meaning of all these botanical indicators is obvious: sex for sale.

What are we to interpret of the artist's erotic depictions of boys – and of a particular adolescent in specific? It is a question that has split his interpreters ever since he gained mega-fame in the twentieth century. The complex historical reality is that the artist was neither the queer hero that, for example, Derek Jarman presented on screen in his twentieth-century movie about the artist, nor so completely devout that, as some art historians unbelievably claim, his Boy With a Basket of Fruit is actually a likeness of Jesus.

His early paintings do offer overt sexual suggestions, or even offers. It's as if Caravaggio, then a penniless young creator, aligned with the city's prostitutes, offering himself to survive. In the Uffizi, with this idea in mind, observers might turn to an additional early work, the 1596 masterpiece the god of wine, in which the deity of wine gazes calmly at the spectator as he begins to untie the dark ribbon of his robe.

A several annums following Bacchus, what could have motivated Caravaggio to paint Victorious Cupid for the artistic collector the nobleman, when he was at last growing nearly established with important church commissions? This unholy non-Christian god revives the sexual provocations of his initial works but in a increasingly powerful, unsettling manner. Fifty years afterwards, its hidden meaning seemed obvious: it was a portrait of Caravaggio's companion. A British traveller saw Victorious Cupid in about the mid-seventeenth century and was told its figure has "the physique and countenance of [Caravaggio's|his] owne youth or servant that laid with him". The identity of this boy was Cecco.

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