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A young boy screams while his skull is firmly gripped, a massive digit pressing into his face as his father's mighty hand holds him by the neck. This scene from Abraham's Sacrifice appears in the Uffizi Gallery, evoking distress through Caravaggio's harrowing portrayal of the suffering youth from the scriptural account. It seems as if Abraham, instructed by God to sacrifice his offspring, could break his spinal column with a solitary twist. Yet the father's preferred method involves the silvery grey blade he holds in his other palm, ready to slit Isaac's throat. One certain aspect remains – whomever modeled as Isaac for this breathtaking work demonstrated extraordinary acting ability. There exists not only fear, surprise and pleading in his darkened gaze but also deep sorrow that a guardian could abandon him so utterly.

The artist took a familiar biblical tale and transformed it so fresh and raw that its horrors seemed to unfold directly in front of the viewer

Viewing before the artwork, observers recognize this as a actual face, an precise depiction of a adolescent subject, because the same boy – identifiable by his tousled locks and nearly dark pupils – features in two other works by the master. In every case, that highly emotional visage dominates the composition. In John the Baptist, he peers playfully from the shadows while embracing a ram. In Amor Vincit Omnia, he smirks with a hardness acquired on Rome's streets, his black feathery appendages demonic, a naked adolescent creating riot in a well-to-do dwelling.

Victorious Cupid, presently displayed at a British gallery, constitutes one of the most discomfiting masterpieces ever created. Viewers feel totally disoriented gazing at it. Cupid, whose darts inspire people with often painful longing, is portrayed as a extremely tangible, vividly lit nude figure, straddling toppled-over objects that include stringed instruments, a music manuscript, plate armor and an architect's T-square. This pile of items resembles, deliberately, the geometric and architectural gear scattered across the ground in the German master's engraving Melencolia I – save here, the gloomy disorder is caused by this grinning Cupid and the turmoil he can unleash.

"Love looks not with the vision, but with the mind, / And thus is winged Cupid painted sightless," wrote the Bard, shortly prior to this work was produced around 1601. But the painter's Cupid is not blind. He stares straight at you. That face – ironic and rosy-faced, looking with bold confidence as he poses naked – is the identical one that screams in terror in The Sacrifice of Isaac.

As Michelangelo Merisi da Caravaggio painted his multiple images of the same distinctive-looking kid in Rome at the dawn of the seventeenth century, he was the highly acclaimed sacred painter in a metropolis ignited by Catholic renewal. Abraham's Offering reveals why he was sought to decorate sanctuaries: he could take a scriptural story that had been portrayed numerous times before and render it so new, so raw and physical that the horror seemed to be happening immediately before the spectator.

However there existed a different side to Caravaggio, evident as quickly as he arrived in Rome in the cold season that concluded 1592, as a artist in his initial 20s with no mentor or patron in the city, just talent and boldness. Most of the paintings with which he captured the sacred metropolis's attention were anything but devout. What may be the absolute first resides in the UK's National Gallery. A youth opens his crimson lips in a scream of pain: while stretching out his dirty fingers for a fruit, he has rather been bitten. Boy Bitten By a Lizard is eroticism amid poverty: observers can discern the painter's gloomy chamber reflected in the cloudy liquid of the glass vase.

The boy wears a rose-colored flower in his hair – a symbol of the sex commerce in early modern art. Venetian artists such as Titian and Jacopo Palma portrayed prostitutes holding blooms and, in a painting lost in the WWII but known through images, Caravaggio portrayed a renowned female prostitute, holding a posy to her bosom. The meaning of all these botanical indicators is clear: intimacy for purchase.

How are we to make of the artist's erotic portrayals of youths – and of a particular adolescent in specific? It is a question that has split his commentators since he gained widespread recognition in the 1980s. The complex historical truth is that the painter was not the queer icon that, for example, Derek Jarman presented on film in his 1986 film about the artist, nor so completely pious that, as some artistic historians improbably claim, his Boy With a Basket of Fruit is in fact a portrait of Christ.

His early paintings do make overt erotic suggestions, or even propositions. It's as if Caravaggio, then a penniless youthful artist, aligned with the city's sex workers, offering himself to live. In the Florentine gallery, with this idea in mind, viewers might look to an additional initial work, the 1596 masterwork Bacchus, in which the deity of alcohol stares calmly at the spectator as he begins to untie the dark ribbon of his garment.

A several years after Bacchus, what could have motivated Caravaggio to paint Victorious Cupid for the art patron the nobleman, when he was finally becoming almost respectable with prestigious church commissions? This unholy pagan god resurrects the sexual provocations of his early works but in a increasingly powerful, unsettling manner. Fifty years afterwards, its secret seemed clear: it was a portrait of Caravaggio's lover. A British traveller viewed 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 laid with him". The name of this boy was Cecco.

The painter had been dead for about forty years when this account was documented.