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A young lad screams while his head is firmly gripped, a massive digit pressing into his cheek as his father's mighty palm grasps him by the throat. This moment from The Sacrifice of Isaac visits the Florentine museum, creating distress through Caravaggio's harrowing portrayal of the tormented child from the biblical narrative. The painting appears as if Abraham, instructed by the Divine to sacrifice his son, could break his neck with a solitary twist. However Abraham's chosen method involves the silvery steel blade he holds in his other hand, ready to cut Isaac's throat. One definite element remains – whoever posed as the sacrifice for this breathtaking work demonstrated extraordinary expressive ability. There exists not only dread, shock and begging in his shadowed gaze but additionally deep grief that a protector could betray him so completely.

The artist adopted a well-known scriptural story and transformed it so vibrant and visceral that its horrors seemed to happen right in front of the viewer

Standing before the painting, viewers recognize this as a actual face, an precise record of a young subject, because the same boy – identifiable by his disheveled locks and nearly black pupils – features in several other paintings by the master. In every instance, that richly expressive visage commands the scene. In John the Baptist, he gazes playfully from the darkness while embracing a ram. In Victorious Cupid, he smirks with a toughness learned on the city's streets, his black feathery appendages sinister, a naked adolescent running riot in a affluent residence.

Victorious Cupid, currently displayed at a London gallery, constitutes one of the most embarrassing masterpieces ever painted. Viewers feel completely unsettled gazing at it. The god of love, whose darts fill people with often agonizing desire, is portrayed as a very tangible, brightly lit nude form, straddling toppled-over objects that include musical instruments, a musical score, plate armour and an architect's T-square. This pile of items echoes, intentionally, the geometric and construction gear strewn across the ground in the German master's engraving Melencolia I – except in this case, the melancholic mess is created by this grinning Cupid and the turmoil he can release.

"Affection sees not with the vision, but with the soul, / And therefore is feathered Cupid painted sightless," wrote the Bard, shortly prior to this work was produced around 1601. But the painter's god is not blind. He stares straight at the observer. That countenance – ironic and rosy-cheeked, staring with brazen assurance as he struts naked – is the identical one that shrieks in terror in Abraham's Test.

When Michelangelo Merisi da Caravaggio painted his multiple images of the same distinctive-looking youth in the Eternal City at the dawn of the 17th century, he was the most celebrated religious artist in a city ignited by Catholic renewal. Abraham's Offering reveals why he was commissioned to decorate sanctuaries: he could adopt a scriptural narrative that had been depicted numerous times before and make it so fresh, so unfiltered and visceral that the terror appeared to be happening directly before you.

However there was another aspect to Caravaggio, evident as soon as he came in Rome in the winter that ended 1592, as a artist in his initial twenties with no teacher or patron in the city, just talent and boldness. The majority of the paintings with which he caught the sacred city's attention were everything but holy. What may be the absolute first hangs in London's National Gallery. A youth parts his crimson mouth in a yell of pain: while reaching out his dirty digits for a fruit, he has rather been bitten. Boy Bitten By a Lizard is sensuality amid poverty: observers can see the painter's dismal room reflected in the cloudy waters of the transparent container.

The boy wears a pink blossom in his coiffure – a symbol of the sex trade in Renaissance painting. Venetian painters such as Titian and Palma Vecchio depicted prostitutes holding flowers and, in a work lost in the second world war but documented through photographs, Caravaggio portrayed a famous female courtesan, holding a posy to her bosom. The message of all these botanical signifiers is clear: sex for purchase.

How are we to make of Caravaggio's sensual depictions of youths – and of one boy in specific? It is a inquiry that has split his commentators since he achieved widespread recognition in the twentieth century. The complex historical reality is that the artist was neither the queer hero that, for example, Derek Jarman put on screen in his 1986 film about the artist, nor so entirely pious that, as some artistic historians improbably assert, his Youth Holding Fruit is in fact a portrait of Jesus.

His early works indeed make explicit sexual implications, or including offers. It's as if Caravaggio, then a destitute youthful artist, identified with the city's sex workers, offering himself to survive. In the Florentine gallery, with this idea in consideration, viewers might look to an additional initial creation, the 1596 masterwork Bacchus, in which the deity of alcohol gazes coolly at the spectator as he begins to untie the black ribbon of his garment.

A few annums following Bacchus, what could have motivated the artist to paint Victorious Cupid for the art collector the nobleman, when he was at last growing nearly established with important ecclesiastical projects? This profane pagan god resurrects the erotic challenges of his initial paintings but in a increasingly intense, unsettling manner. Fifty years afterwards, its hidden meaning seemed obvious: it was a portrait of the painter's companion. A British visitor viewed Victorious Cupid in about the mid-seventeenth century and was informed its subject has "the physique and countenance of [Caravaggio's|his] owne youth or assistant that laid with him". The name of this boy was Francesco.

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