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A youthful lad screams while his head is forcefully held, a massive digit pressing into his face as his parent's mighty hand grasps him by the neck. This scene from The Sacrifice of Isaac visits the Florentine museum, evoking unease through Caravaggio's harrowing portrayal of the suffering youth from the biblical narrative. It seems as if the patriarch, instructed by the Divine to kill his offspring, could snap his neck with a solitary turn. However Abraham's preferred method involves the silvery steel knife he grips in his remaining hand, prepared to slit Isaac's throat. A definite aspect remains – whomever posed as the sacrifice for this breathtaking work displayed remarkable expressive ability. There exists not just fear, shock and pleading in his shadowed eyes but additionally profound grief that a protector could abandon him so completely.

He adopted a familiar scriptural story and made it so fresh and visceral that its horrors seemed to unfold right in view of the viewer

Viewing in front of the painting, observers identify this as a actual countenance, an accurate record of a adolescent subject, because the same boy – recognizable by his disheveled locks and nearly dark eyes – appears in several other paintings by the master. In each case, that richly expressive visage dominates the scene. In John the Baptist, he peers playfully from the shadows while embracing a ram. In Victorious Cupid, he grins with a hardness acquired on the city's streets, his black plumed wings sinister, a naked child creating chaos in a well-to-do residence.

Victorious Cupid, presently displayed at a British museum, represents one of the most embarrassing artworks ever created. Observers feel totally disoriented gazing at it. Cupid, whose arrows inspire people with frequently agonizing desire, is shown as a extremely real, vividly illuminated nude form, standing over overturned objects that include stringed devices, a musical score, metal armor and an builder's T-square. This pile of possessions resembles, deliberately, the geometric and construction gear strewn across the ground in the German master's engraving Melencolia I – except in this case, the melancholic mess is created by this grinning Cupid and the mayhem he can unleash.

"Affection sees not with the eyes, but with the soul, / And thus is winged Love painted sightless," wrote Shakespeare, just prior to this painting was created around the early 1600s. But the painter's Cupid is not blind. He gazes directly at the observer. That countenance – ironic and ruddy-faced, looking with bold assurance as he struts unclothed – is the identical one that shrieks in terror in Abraham's Test.

When Michelangelo Merisi da Caravaggio created his multiple portrayals of the identical distinctive-looking kid in Rome at the dawn of the seventeenth century, he was the highly acclaimed religious artist in a city ignited by Catholic renewal. Abraham's Offering reveals why he was sought to adorn sanctuaries: he could adopt a biblical story that had been depicted many times previously and render it so fresh, so unfiltered and physical that the terror appeared to be happening immediately before the spectator.

Yet there was another aspect to Caravaggio, apparent as soon as he arrived in the capital in the cold season that ended 1592, as a painter in his initial 20s with no mentor or patron in the city, only skill and boldness. Most of the works with which he caught the holy metropolis's attention were anything but holy. What may be the absolute earliest hangs in London's National Gallery. A youth opens his crimson lips in a scream of agony: while reaching out his dirty fingers for a cherry, he has rather been attacked. Boy Bitten By a Lizard is sensuality amid poverty: viewers can discern Caravaggio's gloomy chamber mirrored in the cloudy waters of the glass container.

The boy sports a rose-colored flower in his hair – a emblem of the sex commerce in early modern art. Northern Italian painters such as Tiziano and Palma Vecchio portrayed prostitutes holding blooms and, in a painting destroyed in the WWII but documented through photographs, the master represented a renowned woman courtesan, clutching a bouquet to her chest. The meaning of all these botanical signifiers is clear: intimacy for sale.

What are we to interpret of the artist's sensual depictions of boys – and of one adolescent in specific? It is a question that has split his interpreters since he gained mega-fame in the twentieth century. The complicated past truth is that the artist was not the homosexual icon that, for instance, the filmmaker put on film in his 1986 film Caravaggio, nor so entirely devout that, as certain artistic scholars improbably claim, his Boy With a Basket of Fruit is in fact a portrait of Jesus.

His early works do make overt erotic implications, or even offers. It's as if Caravaggio, then a penniless youthful creator, identified with Rome's prostitutes, offering himself to live. In the Florentine gallery, with this idea in mind, observers might turn to another early creation, the 1596 masterwork Bacchus, in which the deity of wine gazes calmly at you as he begins to undo the dark sash of his garment.

A few annums following the wine deity, what could have driven the artist to create Victorious Cupid for the artistic collector the nobleman, when he was at last growing almost established with prestigious ecclesiastical commissions? This profane non-Christian deity revives the erotic provocations of his early paintings but in a more intense, uneasy manner. Half a century later, its hidden meaning seemed clear: it was a representation of Caravaggio's companion. A English visitor saw Victorious Cupid in about the mid-seventeenth century and was informed its figure has "the physique and countenance of [Caravaggio's|his] own youth or assistant that laid with him". The name of this adolescent was Cecco.

The painter had been deceased for about 40 years when this account was documented.