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A young boy cries out as his skull is forcefully gripped, a massive digit digging into his face as his father's powerful palm holds him by the throat. That moment from The Sacrifice of Isaac appears in the Florentine museum, evoking distress through the artist's chilling rendition of the suffering child from the biblical narrative. It appears as if the patriarch, commanded by God to kill his son, could break his neck with a single turn. However Abraham's chosen method involves the metallic grey blade he grips in his remaining hand, ready to cut Isaac's throat. One certain element stands out – whomever modeled as the sacrifice for this breathtaking piece demonstrated remarkable acting ability. There exists not only dread, shock and pleading in his darkened eyes but also deep sorrow that a protector could betray him so completely.

The artist adopted a familiar biblical story and made it so vibrant and visceral that its horrors appeared to happen directly in front of the viewer

Viewing before the painting, observers recognize this as a actual countenance, an accurate depiction of a young model, because the same boy – recognizable by his tousled hair and nearly dark pupils – features in two other paintings by the master. In each case, that highly emotional face commands the scene. In Youth With a Ram, he gazes mischievously from the darkness while holding a ram. In Victorious Cupid, he smirks with a hardness learned on Rome's streets, his black plumed wings demonic, a naked child running riot in a well-to-do dwelling.

Victorious Cupid, presently displayed at a British museum, constitutes one of the most discomfiting masterpieces ever created. Observers feel completely unsettled gazing at it. Cupid, whose arrows inspire people with frequently painful longing, is portrayed as a extremely real, brightly lit unclothed form, straddling overturned objects that include stringed instruments, a music manuscript, plate armour and an builder's ruler. This pile of possessions echoes, deliberately, the geometric and construction equipment scattered across the ground in Albrecht Dürer's engraving Melencolia I – except in this case, the melancholic disorder is caused by this smirking deity and the mayhem he can unleash.

"Affection sees not with the vision, but with the mind, / And therefore is feathered Cupid painted blind," wrote Shakespeare, shortly before this painting was created around the early 1600s. But Caravaggio's Cupid is not unseeing. He stares directly at you. That face – sardonic and ruddy-cheeked, looking with bold confidence as he struts unclothed – is the identical one that screams in fear in The Sacrifice of Isaac.

When Michelangelo Merisi da Caravaggio created his multiple portrayals of the same distinctive-looking youth in Rome at the dawn of the seventeenth century, he was the highly acclaimed sacred painter in a city enflamed by Catholic renewal. Abraham's Offering demonstrates why he was commissioned to adorn churches: he could adopt a biblical narrative that had been depicted numerous occasions previously and render it so fresh, so raw and physical that the horror appeared to be happening immediately in front of the spectator.

However there was a different aspect to Caravaggio, evident as quickly as he came in the capital in the winter that ended the sixteenth century, as a artist in his initial twenties with no mentor or patron in the urban center, just talent and audacity. Most of the paintings with which he captured the holy metropolis's eye were anything but devout. What could be the absolute earliest hangs in London's National Gallery. A youth parts his crimson mouth in a scream of agony: while reaching out his filthy fingers for a fruit, he has instead been bitten. Boy Bitten By a Lizard is sensuality amid poverty: observers can discern the painter's gloomy room mirrored in the murky liquid of the glass container.

The boy wears a rose-colored flower in his hair – a emblem of the erotic commerce in Renaissance art. Venetian artists such as Titian and Jacopo Palma portrayed courtesans grasping blooms and, in a painting lost in the second world war but known through photographs, Caravaggio represented a renowned woman prostitute, holding a posy to her chest. The meaning of all these botanical indicators is obvious: intimacy for purchase.

What are we to interpret of the artist's sensual portrayals of youths – and of one adolescent in particular? It is a inquiry that has split his commentators since he achieved widespread recognition in the 1980s. The complex historical truth is that the artist was neither the homosexual hero that, for example, the filmmaker presented on screen in his twentieth-century film Caravaggio, nor so completely devout that, as certain artistic historians improbably claim, his Youth Holding Fruit is in fact a likeness of Jesus.

His initial works indeed make explicit erotic implications, or even offers. It's as if Caravaggio, then a penniless young artist, identified with Rome's sex workers, offering himself to survive. In the Florentine gallery, with this thought in consideration, viewers might look to another early creation, the sixteenth-century masterpiece Bacchus, in which the deity of wine stares calmly at the spectator as he begins to untie the black sash of his robe.

A several annums following the wine deity, what could have driven the artist to create Victorious Cupid for the art patron the nobleman, when he was finally becoming almost established with important church commissions? This unholy non-Christian deity resurrects the sexual challenges of his initial paintings but in a increasingly powerful, unsettling way. Fifty years afterwards, its hidden meaning seemed obvious: it was a portrait of Caravaggio's companion. A British visitor saw Victorious Cupid in about the mid-seventeenth century and was informed its subject has "the body & face of [Caravaggio's|his] owne youth or assistant that slept with him". The identity of this boy was Francesco.

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