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The youthful boy screams as his skull is forcefully gripped, a large thumb pressing into his cheek as his father's powerful palm holds him by the neck. That moment from Abraham's Sacrifice appears in the Florentine museum, evoking unease through the artist's chilling rendition of the suffering child from the scriptural narrative. It seems as if Abraham, instructed by God to kill his son, could snap his neck with a single turn. However Abraham's chosen approach involves the silvery steel blade he holds in his other hand, ready to slit the boy's throat. One definite element remains – whomever modeled as Isaac for this astonishing work displayed remarkable acting ability. Within exists not only fear, shock and pleading in his shadowed gaze but also profound grief that a guardian could abandon him so completely.

The artist adopted a well-known biblical story and made it so fresh and raw that its horrors seemed to happen right in front of you

Standing in front of the painting, observers identify this as a real countenance, an precise record of a adolescent subject, because the same boy – recognizable by his disheveled hair and almost dark eyes – appears in several other paintings by the master. In each case, that highly emotional face commands the composition. In John the Baptist, he peers playfully from the darkness while embracing a ram. In Amor Vincit Omnia, he grins with a toughness learned on the city's alleys, his black plumed appendages demonic, a unclothed child running chaos in a well-to-do residence.

Victorious Cupid, presently displayed at a British gallery, constitutes one of the most embarrassing masterpieces ever created. Observers feel totally disoriented gazing at it. The god of love, whose arrows inspire people with often agonizing longing, is portrayed as a extremely real, brightly illuminated nude figure, standing over toppled-over objects that include stringed instruments, a musical score, metal armour and an architect's T-square. This pile of possessions echoes, intentionally, the geometric and construction equipment strewn across the floor in the German master's engraving Melencolia I – except here, the gloomy disorder is caused by this smirking deity and the mayhem he can unleash.

"Affection looks not with the eyes, but with the soul, / And therefore is feathered Cupid painted sightless," penned Shakespeare, shortly prior to this painting was created around the early 1600s. But the painter's Cupid is not unseeing. He stares straight at you. That face – sardonic and rosy-faced, looking with brazen assurance as he struts naked – is the identical one that screams in terror in Abraham's Test.

As Michelangelo Merisi da Caravaggio painted his multiple images of the same unusual-looking kid in the Eternal City at the start of the 17th century, he was the highly acclaimed religious artist in a metropolis ignited by religious revival. Abraham's Offering demonstrates why he was sought to decorate sanctuaries: he could take a scriptural narrative that had been portrayed numerous occasions previously and make it so new, so unfiltered and physical that the terror appeared to be happening directly before you.

Yet there existed another side to the artist, evident as soon as he came in Rome in the winter that concluded the sixteenth century, as a painter in his initial twenties with no teacher or patron in the urban center, just talent and audacity. The majority of the works with which he captured the sacred city's attention were anything but devout. That could be the very first resides in the UK's National Gallery. A youth parts his crimson mouth in a yell of pain: while stretching out his filthy fingers for a fruit, he has instead been attacked. Youth Bitten by a Reptile is eroticism amid poverty: viewers can discern Caravaggio's gloomy chamber mirrored in the cloudy liquid of the glass container.

The adolescent wears a rose-colored flower in his hair – a symbol of the sex commerce in Renaissance painting. Venetian artists such as Tiziano and Palma Vecchio depicted courtesans grasping flowers and, in a painting lost in the second world war but known through images, Caravaggio represented a famous woman prostitute, clutching a bouquet to her chest. The meaning of all these floral signifiers is clear: sex for sale.

What are we to make of Caravaggio's sensual portrayals of youths – and of one adolescent in specific? It is a question that has divided his commentators since he gained widespread recognition in the 1980s. The complicated historical reality is that the artist was not the queer hero that, for instance, Derek Jarman presented on screen in his twentieth-century movie about the artist, nor so completely devout that, as certain artistic scholars improbably assert, his Boy With a Basket of Fruit is actually a likeness of Christ.

His initial paintings do make overt erotic implications, or including propositions. It's as if Caravaggio, then a penniless young creator, aligned with Rome's prostitutes, offering himself to live. In the Uffizi, with this thought in consideration, observers might look to an additional initial work, the 1596 masterpiece the god of wine, in which the god of wine stares calmly at the spectator as he begins to untie the black ribbon of his garment.

A few years after Bacchus, what could have driven the artist to create Amor Vincit Omnia for the artistic patron the nobleman, when he was finally becoming nearly established with prestigious ecclesiastical projects? This profane non-Christian god resurrects the erotic challenges of his early paintings but in a increasingly powerful, uneasy way. Half a century afterwards, its hidden meaning seemed obvious: it was a representation of the painter's companion. A British visitor saw Victorious Cupid in about the mid-seventeenth century and was informed its figure has "the physique and countenance of [Caravaggio's|his] owne youth or servant that slept with him". The name of this adolescent was Francesco.

The painter had been dead for about 40 annums when this account was documented.