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The young boy cries out while his skull is forcefully gripped, a large digit pressing into his face as his father's mighty palm holds him by the throat. That moment from Abraham's Sacrifice visits the Uffizi Gallery, evoking unease through Caravaggio's harrowing rendition of the tormented child from the scriptural account. It seems as if Abraham, instructed by God to kill his son, could snap his spinal column with a solitary turn. Yet the father's preferred method involves the metallic grey blade he grips in his other palm, ready to slit Isaac's throat. A certain element remains – whomever posed as the sacrifice for this astonishing work demonstrated extraordinary expressive ability. Within exists not only dread, surprise and pleading in his darkened gaze but additionally deep sorrow that a protector could abandon him so completely.

The artist took a well-known scriptural tale and made it so fresh and raw that its horrors appeared to unfold right in view of the viewer

Viewing before the painting, observers identify this as a actual face, an accurate depiction of a young model, because the same boy – recognizable by his tousled hair and almost dark pupils – features in two additional works by the master. In every instance, that highly emotional face commands the scene. In John the Baptist, he gazes playfully from the darkness while embracing a lamb. In Victorious Cupid, he grins with a toughness acquired on Rome's alleys, his dark feathery wings demonic, a naked adolescent creating chaos in a well-to-do dwelling.

Victorious Cupid, currently exhibited at a British museum, constitutes one of the most embarrassing artworks ever painted. Observers feel completely disoriented looking at it. The god of love, whose darts inspire people with frequently painful longing, is portrayed as a extremely tangible, vividly illuminated unclothed figure, straddling toppled-over items that include musical devices, a music score, metal armour and an architect's ruler. This heap of items echoes, deliberately, the mathematical and construction equipment strewn across the ground in the German master's engraving Melancholy – save here, the gloomy disorder is caused by this grinning deity and the mayhem he can unleash.

"Affection looks not with the vision, but with the soul, / And thus is winged Love painted blind," penned Shakespeare, shortly before this work was created around the early 1600s. But the painter's Cupid is not blind. He stares directly at the observer. That countenance – sardonic and rosy-faced, staring with brazen assurance as he struts naked – is the identical one that shrieks in fear in Abraham's Test.

As the Italian master painted his multiple images of the identical unusual-appearing kid in Rome at the dawn of the seventeenth century, he was the highly acclaimed religious painter in a metropolis enflamed by religious renewal. Abraham's Offering demonstrates why he was sought to decorate churches: he could adopt a biblical narrative that had been portrayed numerous occasions before and make it so fresh, so unfiltered and visceral that the terror seemed to be occurring immediately in front of the spectator.

Yet there existed another side to Caravaggio, evident as soon as he arrived in the capital in the winter that concluded 1592, as a painter in his initial twenties with no mentor or supporter in the urban center, only skill and boldness. Most of the paintings with which he captured the sacred metropolis's eye were everything but holy. That could be the very earliest hangs in the UK's National Gallery. A youth opens his crimson mouth in a yell of pain: while reaching out his dirty fingers for a fruit, he has instead been bitten. Boy Bitten By a Lizard is sensuality amid poverty: viewers can see the painter's dismal chamber mirrored in the murky liquid of the glass vase.

The adolescent wears a rose-colored flower in his coiffure – a symbol of the sex trade in early modern art. Northern Italian painters such as Titian and Palma Vecchio depicted courtesans grasping flowers and, in a painting destroyed in the WWII but documented through photographs, Caravaggio portrayed a famous woman courtesan, holding a bouquet to her bosom. The message of all these botanical signifiers is obvious: sex for sale.

How are we to make of Caravaggio's erotic portrayals of boys – and of a particular boy in specific? It is a question that has split his interpreters ever since he gained mega-fame in the 1980s. The complex historical truth is that the artist was not the queer hero that, for instance, the filmmaker presented on screen in his twentieth-century film about the artist, nor so completely pious that, as certain art historians unbelievably claim, his Boy With a Basket of Fruit is actually a likeness of Christ.

His early works do offer overt sexual implications, or even offers. It's as if the painter, then a destitute young creator, aligned with Rome's prostitutes, selling himself to live. In the Florentine gallery, with this thought in mind, observers might turn to an additional early creation, the sixteenth-century masterwork Bacchus, in which the god of wine stares coolly at you as he begins to untie the black ribbon of his robe.

A few annums after the wine deity, what could have motivated Caravaggio to paint Victorious Cupid for the artistic patron the nobleman, when he was finally becoming nearly established with prestigious church projects? This profane non-Christian deity revives the erotic challenges of his initial works but in a more powerful, uneasy way. Half a century later, its hidden meaning seemed clear: it was a portrait of the painter's lover. A English visitor saw the painting in about the mid-seventeenth century and was informed its subject has "the physique and countenance of [Caravaggio's|his] own youth or servant that laid with him". The name of this boy was Cecco.

The painter had been deceased for about 40 years when this story was recorded.