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The youthful boy cries out while his head is firmly gripped, a large thumb pressing into his cheek as his parent's mighty palm holds him by the neck. That moment from Abraham's Sacrifice appears in the Uffizi Gallery, creating distress through Caravaggio's harrowing rendition of the tormented youth from the biblical account. It seems as if the patriarch, commanded by God to kill his offspring, could snap his spinal column with a single twist. Yet the father's chosen approach involves the silvery steel knife he grips in his other palm, prepared to cut the boy's neck. One certain element remains – whomever modeled as Isaac for this astonishing piece displayed remarkable expressive skill. There exists not only fear, shock and begging in his shadowed gaze but also profound grief that a guardian could betray him so utterly.

He adopted a familiar scriptural story and made it so fresh and raw that its horrors appeared to happen directly in front of the viewer

Viewing before the painting, observers identify this as a actual countenance, an precise record of a adolescent subject, because the same youth – identifiable by his disheveled locks and nearly black pupils – appears in two other paintings by the master. In every instance, that highly emotional visage dominates the composition. In Youth With a Ram, he peers mischievously from the darkness while holding a ram. In Victorious Cupid, he smirks with a toughness acquired on the city's alleys, his dark feathery wings sinister, a naked adolescent creating riot in a affluent residence.

Victorious Cupid, presently exhibited at a London museum, constitutes one of the most embarrassing masterpieces ever created. Viewers feel totally unsettled gazing at it. The god of love, whose arrows fill people with often painful desire, is shown as a extremely real, vividly illuminated nude figure, standing over toppled-over items that include stringed devices, a music manuscript, plate armor and an builder's ruler. This heap of items resembles, deliberately, the geometric and architectural equipment scattered across the floor in the German master's print Melencolia I – except here, the gloomy disorder is caused by this smirking deity and the mayhem he can release.

"Affection looks not with the eyes, but with the soul, / And thus is feathered Love depicted blind," wrote the Bard, just prior to this painting was created around the early 1600s. But Caravaggio's Cupid is not unseeing. He stares straight at you. That countenance – sardonic and rosy-faced, looking with brazen assurance as he struts naked – is the same one that screams in terror in Abraham's Test.

As Michelangelo Merisi da Caravaggio painted his multiple portrayals of the identical distinctive-appearing youth in the Eternal City at the start of the 17th century, he was the highly acclaimed sacred artist in a metropolis enflamed by Catholic revival. Abraham's Offering demonstrates why he was commissioned to decorate churches: he could take a scriptural story that had been depicted many occasions previously and render it so fresh, so raw and physical that the terror seemed to be happening directly before the spectator.

Yet there existed another aspect to the artist, apparent as soon as he came in Rome in the winter that concluded the sixteenth century, as a artist in his early 20s with no mentor or patron in the city, only skill and boldness. The majority of the paintings with which he captured the sacred city's eye were anything but holy. That could be the very earliest resides in London's National Gallery. A youth parts his red lips in a scream of agony: while stretching out his dirty digits for a fruit, he has rather been bitten. Boy Bitten By a Lizard is eroticism amid squalor: viewers can discern the painter's dismal chamber reflected in the cloudy liquid of the glass vase.

The boy sports a rose-colored flower in his hair – a symbol of the sex trade in early modern painting. Venetian painters such as Tiziano and Jacopo Palma portrayed courtesans holding flowers and, in a work lost in the second world war but known through images, Caravaggio portrayed a famous female prostitute, clutching a posy to her chest. The meaning of all these botanical indicators is obvious: sex for sale.

How are we to make of Caravaggio's sensual depictions of youths – and of a particular boy in particular? It is a inquiry that has divided his interpreters ever since he gained mega-fame in the twentieth century. The complicated historical truth is that the artist was neither the queer icon that, for instance, Derek Jarman put on screen in his twentieth-century movie Caravaggio, nor so entirely pious that, as some art scholars improbably assert, his Boy With a Basket of Fruit is in fact a portrait of Jesus.

His early paintings do offer overt sexual suggestions, or even offers. It's as if Caravaggio, then a destitute youthful artist, aligned with the city's sex workers, offering himself to survive. In the Florentine gallery, with this thought in mind, viewers might turn to another early creation, the 1596 masterwork the god of wine, in which the god of wine stares calmly at the spectator as he begins to untie the black sash of his robe.

A several years following Bacchus, what could have driven Caravaggio to create Victorious Cupid for the art patron the nobleman, when he was finally becoming nearly established with prestigious church projects? This unholy pagan god revives the sexual challenges of his early works but in a increasingly intense, uneasy way. Half a century afterwards, its hidden meaning seemed clear: it was a representation of Caravaggio's companion. A British traveller viewed the painting in about 1649 and was told its figure has "the body & face of [Caravaggio's|his] owne boy or servant that slept with him". The name of this boy was Francesco.

The artist had been dead for about forty annums when this account was documented.