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The youthful boy cries out while his skull is firmly gripped, a massive digit digging into his cheek as his parent's mighty palm holds him by the neck. That moment from The Sacrifice of Isaac appears in the Uffizi Gallery, creating unease through Caravaggio's harrowing portrayal of the tormented child from the biblical narrative. It seems as if Abraham, commanded by God to sacrifice his offspring, could break his spinal column with a solitary turn. Yet Abraham's chosen approach involves the silvery grey blade he grips in his remaining palm, prepared to slit the boy's neck. A definite aspect remains – whomever posed as the sacrifice for this astonishing piece displayed extraordinary expressive skill. Within exists not only fear, surprise and pleading in his darkened gaze but additionally deep grief that a protector could abandon him so completely.

He adopted a familiar biblical tale and transformed it so fresh and visceral that its terrors appeared to happen directly in front of the viewer

Standing before the artwork, viewers recognize this as a real countenance, an precise depiction of a young model, because the same boy – identifiable by his disheveled locks and nearly dark pupils – features in several additional works by the master. In each instance, that richly emotional visage dominates the scene. In Youth With a Ram, he peers mischievously from the darkness while holding a ram. In Amor Vincit Omnia, he smirks with a toughness learned on the city's streets, his dark feathery wings demonic, a unclothed adolescent creating chaos in a well-to-do residence.

Victorious Cupid, presently displayed at a British gallery, represents one of the most discomfiting masterpieces ever created. Observers feel completely disoriented looking at it. The god of love, whose arrows fill people with often painful desire, is shown as a very tangible, vividly lit unclothed figure, straddling toppled-over objects that include stringed instruments, a music manuscript, plate armour and an architect's ruler. This heap of items echoes, deliberately, the mathematical and construction gear strewn across the floor in the German master's print Melencolia I – except in this case, the melancholic mess is caused by this smirking Cupid and the mayhem he can unleash.

"Affection looks not with the eyes, but with the soul, / And therefore is feathered Cupid painted blind," wrote Shakespeare, just before this work was produced around 1601. But Caravaggio's god is not unseeing. He gazes straight at you. That face – sardonic and ruddy-cheeked, looking with brazen assurance as he poses naked – is the identical one that screams in terror in The Sacrifice of Isaac.

When Michelangelo Merisi da Caravaggio created his three portrayals of the identical distinctive-appearing kid in Rome at the dawn of the 17th century, he was the highly acclaimed religious artist in a metropolis ignited by Catholic revival. The Sacrifice of Isaac reveals why he was commissioned to decorate sanctuaries: he could take a biblical narrative that had been portrayed many times previously and render it so new, so unfiltered and visceral that the horror appeared to be happening directly before the spectator.

However there was a different aspect to Caravaggio, evident as quickly as he arrived in the capital in the cold season that ended 1592, as a artist in his initial twenties with no teacher or patron in the city, just skill and boldness. The majority of the paintings with which he captured the holy metropolis's attention were anything but devout. That may be the absolute earliest resides in London's National Gallery. A youth opens his red mouth in a scream of agony: while reaching out his filthy digits for a cherry, he has instead been bitten. Youth Bitten by a Reptile is eroticism amid poverty: viewers can see Caravaggio's dismal room reflected in the cloudy liquid of the transparent container.

The boy wears a rose-colored blossom in his coiffure – a symbol of the erotic commerce in Renaissance art. Venetian painters such as Titian and Jacopo Palma depicted prostitutes grasping flowers and, in a painting lost in the second world war but documented through photographs, Caravaggio represented a renowned female courtesan, clutching a bouquet to her bosom. The message of all these floral indicators is obvious: intimacy for purchase.

How are we to make of Caravaggio's erotic depictions of youths – and of a particular boy in specific? It is a inquiry that has divided his commentators since he achieved widespread recognition in the twentieth century. The complicated past reality is that the painter was not the queer icon that, for example, the filmmaker presented on screen in his 1986 movie about the artist, nor so completely devout that, as certain artistic scholars unbelievably claim, his Boy With a Basket of Fruit is in fact a portrait of Christ.

His early works do offer explicit sexual implications, or including propositions. It's as if Caravaggio, then a destitute youthful creator, identified with the city's sex workers, offering himself to survive. In the Florentine gallery, with this idea in consideration, observers might turn to an additional early creation, the sixteenth-century masterpiece the god of wine, in which the deity of wine stares calmly at the spectator as he starts to undo the black sash of his garment.

A several annums following the wine deity, what could have driven the artist to paint Amor Vincit Omnia for the artistic patron Vincenzo Giustiniani, when he was at last becoming almost respectable with prestigious ecclesiastical projects? This profane non-Christian deity revives the erotic challenges of his initial works but in a increasingly powerful, unsettling manner. Half a century afterwards, its hidden meaning seemed obvious: it was a representation of Caravaggio's companion. A English visitor viewed the painting 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 identity of this boy was Francesco.

The artist had been deceased for about 40 years when this story was documented.