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A youthful boy cries out as his skull is forcefully gripped, a massive thumb pressing into his cheek as his father's mighty palm grasps him by the throat. This scene from The Sacrifice of Isaac visits the Florentine museum, creating unease through the artist's chilling rendition of the tormented youth from the biblical account. The painting appears as if Abraham, instructed by the Divine to sacrifice his offspring, could snap his neck with a solitary twist. Yet the father's preferred method involves the silvery grey blade he holds in his other palm, prepared to slit Isaac's throat. One certain aspect stands out – whomever posed as Isaac for this astonishing work displayed remarkable acting ability. There exists not only dread, shock and pleading in his shadowed gaze but additionally deep sorrow that a protector could betray him so utterly.

The artist took a well-known scriptural tale and transformed it so fresh and visceral that its horrors seemed to unfold right in view of you

Viewing in front of the artwork, viewers recognize this as a real face, an precise record of a adolescent subject, because the identical boy – identifiable by his disheveled hair and nearly black pupils – appears in two additional works by Caravaggio. In every case, that highly emotional visage commands the composition. In John the Baptist, he gazes mischievously from the darkness while holding a lamb. In Amor Vincit Omnia, he smirks with a hardness acquired on the city's alleys, his dark feathery appendages demonic, a naked adolescent running riot in a well-to-do residence.

Victorious Cupid, currently exhibited at a British gallery, represents one of the most embarrassing artworks ever painted. Observers feel totally disoriented gazing at it. Cupid, whose arrows inspire people with frequently painful longing, is portrayed as a very tangible, vividly illuminated nude figure, straddling overturned objects that include musical devices, a music manuscript, metal armor and an architect's T-square. This heap of possessions echoes, intentionally, the geometric and construction equipment scattered across the floor in Albrecht Dürer's print Melancholy – except here, the melancholic mess is caused by this grinning Cupid and the turmoil he can release.

"Affection looks not with the vision, but with the soul, / And therefore is winged Cupid painted sightless," wrote the Bard, just before this work was created around 1601. But Caravaggio's Cupid is not blind. He stares straight at you. That face – sardonic and ruddy-cheeked, staring with brazen confidence as he struts unclothed – is the same one that shrieks in fear in Abraham's Test.

As Michelangelo Merisi da Caravaggio created his multiple portrayals of the identical unusual-looking youth in Rome at the start of the seventeenth century, he was the most acclaimed sacred artist in a metropolis ignited by Catholic revival. Abraham's Offering reveals why he was sought to adorn sanctuaries: he could adopt a scriptural narrative that had been portrayed numerous occasions previously and make it so new, so unfiltered and physical that the horror seemed to be occurring directly before you.

Yet there was another side to the artist, evident as quickly as he arrived in Rome in the winter that ended the sixteenth century, as a painter in his initial 20s with no mentor or patron in the city, only skill and boldness. The majority of the works with which he caught the sacred metropolis's eye were anything but devout. That may be the very first resides in the UK's art museum. A youth opens his crimson mouth in a scream of agony: while reaching out his dirty fingers for a fruit, he has rather been bitten. Youth Bitten by a Reptile is eroticism amid squalor: observers can see the painter's gloomy room reflected in the murky waters of the transparent vase.

The adolescent sports a pink flower in his hair – a emblem of the erotic commerce in Renaissance art. Venetian painters such as Tiziano and Palma Vecchio depicted courtesans grasping flowers and, in a painting destroyed in the second world war but documented through photographs, Caravaggio portrayed a renowned woman courtesan, clutching a bouquet to her chest. The meaning of all these floral signifiers is obvious: intimacy for purchase.

How are we to interpret of the artist's erotic portrayals of boys – and of a particular boy in specific? It is a inquiry that has split his commentators ever since he gained widespread recognition in the twentieth century. The complex historical reality is that the painter was not the homosexual hero that, for example, Derek Jarman put on film in his twentieth-century movie Caravaggio, nor so entirely devout that, as some art scholars improbably claim, his Youth Holding Fruit is actually a portrait of Jesus.

His initial works do offer overt erotic implications, or including offers. It's as if Caravaggio, then a penniless young creator, aligned with the city's sex workers, offering himself to survive. In the Uffizi, with this idea in consideration, observers might look to another initial creation, the 1596 masterpiece the god of wine, in which the deity of wine stares calmly at the spectator as he begins to undo the black ribbon of his robe.

A several annums after the wine deity, what could have driven Caravaggio to paint Victorious Cupid for the artistic collector the nobleman, when he was at last growing nearly established with important church projects? This unholy pagan deity resurrects the erotic challenges of his early paintings but in a increasingly powerful, uneasy way. Fifty years afterwards, its hidden meaning seemed clear: it was a representation of the painter's lover. A British traveller viewed the painting in about 1649 and was informed its figure has "the body & face of [Caravaggio's|his] owne boy or assistant that slept with him". The identity of this boy was Cecco.

The artist had been deceased for about 40 annums when this story was documented.