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A youthful boy cries out as his head is forcefully held, a large digit digging into his face as his parent's mighty hand holds him by the throat. This scene from Abraham's Sacrifice visits the Uffizi Gallery, evoking distress through the artist's harrowing rendition of the tormented youth from the scriptural narrative. The painting seems as if Abraham, instructed by the Divine to kill his offspring, could break his spinal column with a solitary twist. However Abraham's chosen approach involves the silvery steel blade he grips in his other hand, prepared to cut Isaac's throat. A certain element remains – whoever modeled as the sacrifice for this breathtaking work demonstrated remarkable expressive skill. Within exists not just fear, shock and pleading in his darkened eyes but additionally profound sorrow that a protector could betray him so utterly.

The artist took a well-known scriptural tale and made it so fresh and raw that its horrors appeared to happen directly in front of you

Standing before the painting, observers identify this as a real countenance, an accurate record of a young subject, because the same boy – identifiable by his tousled hair and nearly black eyes – features in two additional paintings by Caravaggio. In every instance, that richly expressive visage dominates the scene. In Youth With a Ram, he gazes mischievously from the darkness while embracing a ram. In Victorious Cupid, he grins with a toughness learned on the city's streets, his dark plumed appendages sinister, a unclothed child running riot in a affluent dwelling.

Victorious Cupid, presently displayed at a British gallery, represents one of the most embarrassing masterpieces ever painted. Viewers feel totally unsettled gazing at it. The god of love, whose arrows fill people with frequently agonizing longing, is shown as a very real, vividly illuminated unclothed form, straddling overturned objects that comprise stringed devices, a musical score, plate armor and an builder's ruler. This heap of possessions echoes, intentionally, the mathematical and architectural gear strewn across the floor in Albrecht Dürer's print Melencolia I – save here, the gloomy disorder is caused by this grinning Cupid and the mayhem he can unleash.

"Affection sees not with the vision, but with the soul, / And thus is winged Love painted sightless," penned the Bard, just before this painting was produced around 1601. But Caravaggio's god is not unseeing. He gazes straight at the observer. That face – sardonic and rosy-cheeked, looking with bold assurance as he poses unclothed – is the identical one that shrieks in fear in Abraham's Test.

As Michelangelo Merisi da Caravaggio painted his three images of the same unusual-looking kid in Rome at the start of the seventeenth century, he was the highly celebrated religious painter in a metropolis ignited by religious revival. The Sacrifice of Isaac demonstrates why he was commissioned to adorn sanctuaries: he could adopt a biblical story that had been portrayed numerous times before and make it so new, so unfiltered and visceral that the horror appeared to be occurring directly in front of the spectator.

Yet there existed another aspect to the artist, apparent as quickly as he arrived in Rome in the winter that concluded 1592, as a painter in his early twenties with no teacher or patron in the urban center, only talent and audacity. Most of the works with which he caught the sacred city's attention were anything but holy. That may be the absolute first resides in the UK's National Gallery. A young man parts his red lips in a scream of pain: while reaching out his filthy digits for a fruit, he has rather been bitten. Youth Bitten by a Reptile is eroticism amid squalor: observers can see Caravaggio's dismal room reflected in the cloudy liquid of the transparent container.

The boy wears a rose-colored flower in his hair – a emblem of the erotic commerce in early modern painting. Northern Italian painters such as Tiziano and Palma Vecchio depicted courtesans holding flowers and, in a work destroyed in the WWII but known through photographs, Caravaggio portrayed a famous female courtesan, holding a posy to her bosom. The message of all these floral signifiers is obvious: intimacy for sale.

What are we to make of Caravaggio's sensual depictions of youths – and of a particular boy in specific? It is a inquiry that has split his interpreters since he achieved widespread recognition in the twentieth century. The complicated past reality is that the artist was neither the homosexual icon that, for instance, Derek Jarman presented on screen in his twentieth-century movie about the artist, nor so completely devout that, as certain artistic historians improbably assert, his Boy With a Basket of Fruit is actually a portrait of Jesus.

His initial paintings indeed make overt erotic implications, or even offers. It's as if the painter, then a destitute youthful artist, aligned with Rome's prostitutes, offering himself to survive. In the Florentine gallery, with this thought in consideration, observers might look to another initial work, the sixteenth-century masterpiece the god of wine, in which the god of wine gazes calmly at you as he starts to undo the black ribbon of his robe.

A few years following Bacchus, what could have motivated the artist to create Victorious Cupid for the artistic collector the nobleman, when he was at last growing almost respectable with important church commissions? This profane pagan deity resurrects the sexual challenges of his initial paintings but in a increasingly powerful, unsettling way. Half a century later, its hidden meaning seemed obvious: it was a portrait of the painter's companion. A English visitor viewed Victorious Cupid in about 1649 and was told its subject has "the body & face of [Caravaggio's|his] own youth or assistant that laid with him". The identity of this adolescent was Francesco.

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