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A young lad cries out while his head is firmly gripped, a large digit pressing into his cheek as his father's powerful hand holds him by the throat. That moment from Abraham's Sacrifice appears in the Uffizi Gallery, creating unease through Caravaggio's chilling rendition of the tormented child from the biblical account. It appears as if the patriarch, instructed by the Divine to kill his offspring, could break his spinal column with a solitary turn. Yet the father's chosen approach involves the metallic steel knife he holds in his remaining palm, prepared to cut Isaac's neck. One certain aspect remains – whoever posed as the sacrifice for this breathtaking work demonstrated extraordinary acting skill. Within exists not only dread, shock and begging in his darkened eyes but also profound sorrow that a guardian could abandon him so utterly.

The artist adopted a well-known biblical story and made it so vibrant and raw that its terrors seemed to unfold directly in view of the viewer

Viewing before the painting, viewers recognize this as a real countenance, an accurate record of a adolescent model, because the identical boy – recognizable by his tousled hair and nearly dark pupils – appears in several additional works by the master. In each case, that richly emotional face commands the scene. In Youth With a Ram, he peers mischievously from the darkness while holding a lamb. In Amor Vincit Omnia, he smirks with a toughness acquired on the city's alleys, his black feathery wings sinister, a naked adolescent running chaos in a well-to-do residence.

Victorious Cupid, presently exhibited at a London museum, constitutes one of the most embarrassing masterpieces ever painted. Observers feel completely unsettled looking at it. Cupid, whose arrows fill people with frequently painful desire, is portrayed as a very tangible, vividly lit unclothed figure, straddling overturned objects that include musical instruments, a music manuscript, plate armour and an architect's T-square. This heap of possessions echoes, intentionally, the mathematical and architectural gear strewn across the ground in the German master's print Melancholy – except here, the gloomy mess is caused by this grinning Cupid and the mayhem he can release.

"Love looks not with the vision, but with the soul, / And therefore is feathered Love depicted blind," penned Shakespeare, just prior to this work was created around 1601. But the painter's god is not unseeing. He gazes directly at you. That face – sardonic and ruddy-cheeked, staring with brazen confidence as he struts unclothed – is the identical one that shrieks in terror in Abraham's Test.

As Michelangelo Merisi da Caravaggio painted his multiple portrayals of the same unusual-appearing kid in Rome at the start of the seventeenth century, he was the most celebrated sacred painter in a metropolis enflamed by Catholic renewal. The Sacrifice of Isaac demonstrates why he was commissioned to adorn sanctuaries: he could adopt a scriptural story that had been portrayed many times before and render it so fresh, so unfiltered and physical that the terror seemed to be happening immediately in front of the spectator.

However there was a different side to the artist, apparent as quickly as he arrived in Rome in the winter that ended 1592, as a painter in his initial twenties with no mentor or supporter in the urban center, just talent and audacity. Most of the works with which he caught the holy city's attention were everything but holy. That could be the absolute first hangs in the UK's National Gallery. A young man opens his crimson lips in a yell of agony: while stretching out his dirty fingers for a fruit, he has rather been attacked. Youth Bitten by a Reptile is sensuality amid squalor: viewers can discern Caravaggio's dismal room mirrored in the murky waters of the transparent vase.

The adolescent sports a rose-colored flower in his hair – a symbol of the erotic commerce in Renaissance art. Northern Italian artists such as Titian and Jacopo Palma depicted courtesans holding blooms and, in a painting destroyed in the second world war but known through photographs, Caravaggio represented a famous woman courtesan, clutching a posy to her bosom. The message of all these botanical indicators is obvious: sex for sale.

What are we to interpret of the artist's sensual depictions of youths – and of one adolescent in particular? It is a inquiry that has divided his interpreters ever since he gained mega-fame in the twentieth century. The complex past truth is that the painter was neither the homosexual hero that, for instance, the filmmaker put on screen in his 1986 film Caravaggio, nor so completely devout that, as certain art historians unbelievably assert, his Youth Holding Fruit is actually a portrait of Jesus.

His initial works indeed make explicit erotic suggestions, or including offers. It's as if the painter, then a penniless youthful creator, identified with Rome's sex workers, offering himself to live. In the Uffizi, with this idea in mind, observers might turn to an additional early creation, the 1596 masterpiece Bacchus, in which the god of wine gazes coolly at the spectator as he begins to undo the black sash of his garment.

A few annums following the wine deity, what could have motivated Caravaggio to paint Victorious Cupid for the artistic patron Vincenzo Giustiniani, when he was at last becoming almost established with prestigious ecclesiastical projects? This profane non-Christian deity resurrects the erotic provocations of his initial works but in a more intense, uneasy manner. Half a century later, 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 physique and countenance of [Caravaggio's|his] own youth or assistant that laid with him". The name of this boy was Francesco.

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