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The youthful lad cries out while his head is firmly held, a massive digit pressing into his cheek as his father's powerful palm grasps him by the throat. That moment from Abraham's Sacrifice appears in the Uffizi Gallery, creating unease through Caravaggio's harrowing portrayal of the suffering child from the scriptural account. It appears as if Abraham, instructed by God to kill his son, could break his spinal column with a single twist. However Abraham's preferred method involves the silvery steel blade he grips in his other palm, ready to cut Isaac's throat. A certain aspect remains – whomever posed as the sacrifice for this astonishing piece displayed extraordinary expressive skill. There exists not just dread, shock and begging in his shadowed gaze but also profound sorrow that a protector could betray him so completely.

He adopted a familiar biblical tale and transformed it so vibrant and visceral that its terrors appeared to happen directly in view of you

Standing before the painting, observers recognize this as a actual countenance, an precise depiction of a young model, because the same youth – identifiable by his disheveled locks and nearly dark pupils – appears in several additional works by the master. In each instance, that richly expressive visage commands the composition. In John the Baptist, he gazes mischievously from the darkness while holding a ram. In Amor Vincit Omnia, he smirks with a hardness learned on Rome's alleys, his dark feathery appendages demonic, a unclothed adolescent running chaos in a well-to-do dwelling.

Victorious Cupid, presently exhibited at a London museum, represents one of the most discomfiting artworks ever created. Observers feel totally unsettled looking at it. Cupid, whose arrows inspire people with frequently agonizing desire, is shown as a extremely real, brightly lit nude figure, standing over toppled-over objects that comprise stringed instruments, a musical score, plate armour and an architect's ruler. This pile of items resembles, deliberately, the geometric and architectural equipment scattered across the ground in Albrecht Dürer's print Melancholy – except here, the gloomy mess is created by this smirking deity and the turmoil he can unleash.

"Love looks not with the vision, but with the soul, / And therefore is winged Love painted blind," penned the Bard, shortly before this painting was produced around 1601. But Caravaggio's Cupid is not unseeing. He gazes straight at the observer. That face – sardonic and ruddy-faced, looking with bold assurance as he struts unclothed – is the same one that shrieks in fear in Abraham's Test.

As Michelangelo Merisi da Caravaggio created his three images of the identical unusual-looking youth in Rome at the start of the 17th century, he was the most acclaimed religious artist in a metropolis enflamed by Catholic renewal. Abraham's Offering reveals why he was commissioned to adorn churches: he could adopt a scriptural story that had been portrayed many times previously and make it so fresh, so raw and visceral that the terror seemed to be occurring immediately before you.

However there existed another aspect to the artist, evident as soon as he arrived in the capital in the winter that concluded the sixteenth century, as a artist in his early twenties with no teacher or supporter in the city, just talent and audacity. Most of the paintings with which he caught the holy city's attention were everything but devout. That could be the absolute earliest resides in the UK's art museum. A youth opens his crimson lips in a yell of agony: while reaching out his dirty fingers for a fruit, he has instead been attacked. Youth Bitten by a Reptile is sensuality amid poverty: observers can discern the painter's dismal chamber reflected in the cloudy waters of the transparent vase.

The adolescent wears a rose-colored flower in his coiffure – a symbol of the erotic trade in Renaissance painting. Venetian artists such as Tiziano and Jacopo Palma portrayed prostitutes holding flowers and, in a painting destroyed in the second world war but documented through images, the master portrayed a famous female prostitute, holding a bouquet to her bosom. The meaning of all these floral indicators is clear: intimacy for sale.

What are we to make of the artist's erotic portrayals of youths – and of a particular adolescent in specific? It is a question that has split his commentators since he achieved widespread recognition in the 1980s. The complicated historical reality is that the artist was neither the homosexual hero that, for instance, the filmmaker put on screen in his 1986 film Caravaggio, nor so entirely devout that, as certain art scholars unbelievably claim, his Youth Holding Fruit is actually a portrait of Jesus.

His early works do offer overt sexual implications, or including offers. It's as if the painter, then a penniless young creator, identified with the city's sex workers, selling himself to live. In the Uffizi, with this idea in consideration, viewers might turn to an additional early work, the sixteenth-century masterpiece the god of wine, in which the god of wine stares calmly at the spectator as he begins to undo the dark ribbon of his robe.

A several years following Bacchus, what could have motivated the artist to create Amor Vincit Omnia for the artistic patron Vincenzo Giustiniani, when he was finally becoming almost respectable with important church commissions? This profane pagan deity revives the erotic provocations of his early works but in a more powerful, uneasy manner. Fifty years later, its hidden meaning seemed obvious: it was a representation of Caravaggio's companion. A British visitor saw the painting in about 1649 and was informed its figure 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 story was recorded.