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The youthful lad screams while his skull is forcefully gripped, a massive thumb pressing into his cheek as his parent's powerful palm holds him by the neck. That moment from The Sacrifice of Isaac appears in the Uffizi Gallery, evoking unease through Caravaggio's harrowing rendition of the suffering child from the biblical account. It appears as if the patriarch, instructed by God to sacrifice his son, could snap his neck with a solitary twist. However Abraham's preferred method involves the silvery steel knife he grips in his other hand, prepared to cut Isaac's neck. A certain element stands out – whomever posed as Isaac for this astonishing work displayed remarkable acting ability. There exists not only fear, surprise and pleading in his darkened eyes but additionally deep grief that a guardian could abandon him so utterly.

He adopted a familiar biblical story and transformed it so vibrant and raw that its terrors appeared to happen right in view of you

Standing in front of the painting, viewers recognize this as a real countenance, an accurate record of a adolescent subject, because the same youth – recognizable by his tousled hair and almost black pupils – appears in two other works by the master. In each case, that richly expressive visage dominates the composition. In Youth With a Ram, he peers playfully from the darkness while embracing a ram. In Victorious Cupid, he smirks with a toughness acquired on Rome's streets, his dark feathery wings demonic, a naked adolescent creating chaos in a well-to-do dwelling.

Victorious Cupid, currently displayed at a British gallery, constitutes one of the most embarrassing artworks ever painted. Viewers feel totally disoriented gazing at it. The god of love, whose darts inspire people with frequently agonizing desire, is shown as a very real, brightly lit nude figure, straddling toppled-over items that include musical devices, a music manuscript, plate armor and an builder's T-square. This pile of possessions resembles, deliberately, the geometric and construction gear strewn across the floor in the German master's engraving Melencolia I – except here, the melancholic mess is created by this smirking Cupid and the turmoil he can release.

"Love sees not with the eyes, but with the mind, / And thus is feathered Love painted sightless," penned Shakespeare, just prior to this painting was produced around 1601. But Caravaggio's god is not blind. He gazes directly at the observer. That countenance – ironic and ruddy-cheeked, staring with bold assurance as he struts unclothed – is the identical one that screams in fear in Abraham's Test.

When Michelangelo Merisi da Caravaggio painted his three images of the same unusual-appearing kid in the Eternal City at the start of the seventeenth century, he was the most acclaimed sacred painter in a city ignited by Catholic renewal. Abraham's Offering reveals why he was commissioned to adorn churches: he could adopt a scriptural narrative that had been portrayed numerous times previously and make it so new, so raw and visceral that the terror appeared to be happening directly before you.

Yet there was another side to Caravaggio, apparent as soon as he arrived in the capital in the cold season that ended the sixteenth century, as a artist in his initial twenties with no teacher or supporter in the city, only skill and boldness. The majority of the works with which he captured the holy metropolis's attention were anything but devout. That may be the absolute first hangs in the UK's National Gallery. A youth opens his crimson lips in a yell of agony: while stretching out his dirty digits for a fruit, he has rather been bitten. Boy Bitten By a Lizard is eroticism amid poverty: observers can see the painter's gloomy room mirrored in the cloudy liquid of the transparent container.

The boy sports a rose-colored flower in his hair – a symbol of the erotic commerce in Renaissance painting. Northern Italian artists such as Tiziano and Palma Vecchio depicted prostitutes holding flowers and, in a work destroyed in the WWII but known through images, the master represented a famous woman prostitute, clutching a posy to her chest. The message of all these botanical indicators is clear: intimacy for sale.

How are we to interpret of the artist's sensual portrayals of boys – and of a particular boy in specific? It is a question that has divided his interpreters since he gained mega-fame in the twentieth century. The complex historical truth is that the artist was neither the queer hero that, for example, the filmmaker presented on screen in his twentieth-century movie Caravaggio, nor so entirely devout that, as some artistic scholars unbelievably claim, his Boy With a Basket of Fruit is in fact a portrait of Christ.

His early works do make explicit sexual implications, or even propositions. It's as if the painter, then a penniless young creator, identified with the city's sex workers, selling himself to live. In the Florentine gallery, with this idea in mind, viewers might turn to an additional initial creation, the sixteenth-century masterpiece Bacchus, in which the god of wine stares calmly at you as he begins to undo the dark sash of his garment.

A few annums following the wine deity, what could have driven the artist to paint Victorious Cupid for the art collector the nobleman, when he was finally becoming nearly established with prestigious ecclesiastical commissions? This profane non-Christian deity revives the sexual challenges of his initial works but in a increasingly intense, unsettling way. Half a century later, its hidden meaning seemed clear: it was a representation of the painter's lover. A English visitor viewed Victorious Cupid in about 1649 and was informed its figure has "the body & face of [Caravaggio's|his] own boy or assistant that laid with him". The name of this boy was Cecco.

The artist had been deceased for about forty annums when this story was documented.