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The youthful boy cries out as his head is forcefully held, a large thumb pressing into his face as his parent's powerful palm grasps him by the neck. This moment from The Sacrifice of Isaac appears in the Uffizi Gallery, creating unease through Caravaggio's chilling portrayal of the tormented youth from the scriptural account. It seems as if the patriarch, commanded by the Divine to kill his son, could snap his neck with a solitary twist. Yet the father's preferred approach involves the silvery steel blade he grips in his remaining hand, prepared to cut Isaac's throat. A definite aspect remains – whomever modeled as Isaac for this astonishing piece displayed extraordinary expressive ability. There exists not only fear, shock and begging in his darkened eyes but additionally deep grief that a protector could abandon him so completely.

The artist adopted a familiar biblical story and made it so fresh and raw that its horrors appeared to unfold right in view of you

Standing before the artwork, observers recognize this as a real face, an precise record of a adolescent subject, because the same youth – identifiable by his tousled locks and nearly black pupils – appears in two other paintings by the master. In every instance, that highly expressive face commands the composition. In John the Baptist, he gazes playfully from the shadows while embracing a ram. In Amor Vincit Omnia, he smirks with a hardness learned on Rome's streets, his black feathery wings sinister, a unclothed adolescent running riot in a well-to-do dwelling.

Amor Vincit Omnia, presently exhibited at a British museum, constitutes one of the most embarrassing masterpieces ever painted. Observers feel totally disoriented looking at it. Cupid, whose arrows fill people with often agonizing desire, is portrayed as a very real, brightly lit unclothed form, straddling overturned items that include musical devices, a music manuscript, metal armor and an architect's T-square. This pile of items echoes, intentionally, the mathematical and construction gear scattered across the ground in the German master's engraving Melancholy – except in this case, the gloomy disorder is caused by this grinning Cupid and the turmoil he can release.

"Affection sees not with the eyes, but with the soul, / And thus is winged Love painted sightless," wrote the Bard, just before this painting was created around 1601. But Caravaggio's Cupid is not unseeing. He gazes directly at you. That face – ironic and rosy-cheeked, staring with bold assurance as he poses unclothed – is the same one that screams in fear in The Sacrifice of Isaac.

As Michelangelo Merisi da Caravaggio created his three portrayals of the same unusual-appearing youth in the Eternal City at the start of the seventeenth century, he was the highly celebrated religious painter in a city enflamed by religious revival. The Sacrifice of Isaac demonstrates why he was sought to decorate sanctuaries: he could adopt a scriptural narrative that had been portrayed many occasions before and make it so new, so raw and visceral that the horror appeared to be occurring directly before the spectator.

Yet there existed a different side to the artist, evident as quickly as he came in Rome in the cold season that concluded the sixteenth century, as a artist in his initial twenties with no teacher or patron in the urban center, just talent and boldness. Most of the works with which he captured the holy metropolis's eye were anything but devout. What may be the very first hangs in the UK's art museum. A youth opens his red lips in a scream of agony: while reaching out his dirty fingers for a cherry, he has instead been bitten. Youth Bitten by a Reptile is eroticism amid squalor: viewers can discern Caravaggio's dismal room mirrored in the murky liquid of the transparent vase.

The boy sports a rose-colored flower in his hair – a symbol of the erotic trade in Renaissance painting. Northern Italian artists such as Tiziano and Palma Vecchio portrayed courtesans grasping flowers and, in a painting destroyed in the second world war but known through photographs, the master portrayed a renowned female courtesan, holding a posy to her chest. The meaning of all these botanical signifiers is clear: sex for sale.

How are we to interpret of the artist's erotic portrayals of youths – and of a particular adolescent in specific? It is a inquiry that has split his commentators ever since he gained widespread recognition in the 1980s. The complex historical reality is that the artist was neither the homosexual hero that, for instance, the filmmaker presented on screen in his 1986 movie Caravaggio, nor so entirely devout that, as certain art historians improbably claim, his Boy With a Basket of Fruit is in fact a likeness of Christ.

His initial works indeed offer overt sexual suggestions, or even propositions. It's as if Caravaggio, then a penniless youthful creator, identified with Rome's prostitutes, offering himself to live. In the Florentine gallery, with this thought in mind, observers might look to another initial work, the 1596 masterpiece Bacchus, in which the deity of alcohol stares coolly at you as he starts to untie the black sash of his robe.

A several annums after the wine deity, what could have motivated the artist to paint Amor Vincit Omnia for the art patron the nobleman, when he was finally growing nearly established with important church projects? This unholy pagan god resurrects the sexual challenges of his early paintings but in a more powerful, unsettling way. Half a century afterwards, its secret seemed clear: it was a portrait of the painter's companion. A British visitor saw the painting in about 1649 and was informed its subject has "the body & face of [Caravaggio's|his] owne boy or assistant that slept with him". The identity of this adolescent was Francesco.

The painter had been deceased for about forty years when this story was recorded.