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The youthful boy cries out as his skull is firmly gripped, a massive digit digging into his cheek as his parent's mighty palm holds him by the neck. That moment from The Sacrifice of Isaac visits the Uffizi Gallery, evoking distress through the artist's harrowing portrayal of the tormented child from the biblical narrative. The painting appears as if Abraham, instructed by God to sacrifice his son, could break his neck with a single turn. Yet the father's preferred approach involves the silvery grey blade he grips in his remaining palm, ready to cut Isaac's throat. One definite aspect stands out – whomever modeled as Isaac for this breathtaking piece displayed remarkable acting ability. Within exists not just fear, surprise and pleading in his darkened gaze but additionally deep sorrow that a guardian could betray him so completely.

He took a familiar scriptural tale and transformed it so fresh and visceral that its horrors seemed to happen directly in view of you

Standing in front of the artwork, observers recognize this as a actual face, an accurate depiction of a adolescent subject, because the identical boy – identifiable by his tousled hair and almost dark pupils – appears in two additional paintings by the master. In every case, that richly emotional visage commands the composition. In Youth With a Ram, he peers playfully from the darkness while embracing a ram. In Victorious Cupid, he grins with a hardness acquired on the city's streets, his dark feathery appendages sinister, a unclothed child creating riot in a affluent residence.

Victorious Cupid, presently displayed at a British museum, constitutes one of the most embarrassing masterpieces ever created. Viewers feel completely unsettled gazing at it. The god of love, whose arrows inspire people with frequently agonizing desire, is shown as a very tangible, brightly lit nude form, straddling toppled-over items that comprise stringed instruments, a music score, plate armour and an architect's ruler. This pile of possessions echoes, deliberately, the geometric and architectural gear strewn across the ground in the German master's engraving Melencolia I – except in this case, the gloomy disorder 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 feathered Love depicted blind," wrote Shakespeare, shortly before this work was created around 1601. But the painter's Cupid is not blind. He gazes straight at you. That countenance – ironic and ruddy-cheeked, looking with brazen assurance as he struts naked – is the same one that screams in fear in The Sacrifice of Isaac.

When the Italian master painted his three portrayals of the identical unusual-looking kid in the Eternal City at the start of the seventeenth century, he was the highly acclaimed sacred artist in a metropolis ignited by religious revival. The Sacrifice of Isaac reveals why he was commissioned to decorate sanctuaries: he could take a scriptural narrative that had been depicted many times before and render it so new, so raw and physical that the horror appeared to be happening directly before the spectator.

Yet there existed a different aspect to the artist, evident as soon as he came in Rome in the cold season that concluded the sixteenth century, as a artist in his early twenties with no mentor or supporter in the urban center, just skill and boldness. The majority of the paintings with which he caught the holy metropolis's eye were anything but devout. That could be the very first hangs in the UK's National Gallery. A youth parts his red lips in a yell of pain: while reaching out his dirty fingers for a fruit, he has rather been attacked. Youth Bitten by a Reptile is sensuality amid poverty: observers can discern Caravaggio's gloomy chamber mirrored in the murky waters of the transparent vase.

The boy sports a rose-colored flower in his hair – a emblem of the sex commerce in early modern painting. Venetian artists such as Tiziano and Jacopo Palma portrayed prostitutes grasping flowers and, in a work lost in the WWII but known through images, Caravaggio represented a renowned female prostitute, holding a bouquet to her chest. The meaning of all these botanical indicators is obvious: intimacy for sale.

What are we to interpret of the artist's sensual depictions of youths – and of one adolescent in specific? It is a question that has split his commentators since he gained mega-fame in the twentieth century. The complicated historical reality is that the painter was not the homosexual icon that, for instance, the filmmaker put on film in his 1986 movie about the artist, nor so entirely devout that, as some art historians improbably assert, his Boy With a Basket of Fruit is in fact a likeness of Christ.

His initial works do offer overt erotic implications, or even propositions. It's as if the painter, then a destitute young artist, identified with Rome's sex workers, offering himself to live. In the Uffizi, with this idea in mind, viewers might look to another initial creation, the sixteenth-century masterpiece the god of wine, in which the god of wine stares coolly at you as he starts to undo the dark sash of his robe.

A several annums following Bacchus, what could have driven the artist to create Victorious Cupid for the artistic patron Vincenzo Giustiniani, when he was at last becoming almost established with important ecclesiastical projects? This profane non-Christian god resurrects the erotic challenges of his initial works but in a more powerful, unsettling manner. Half a century later, its secret seemed obvious: it was a representation of Caravaggio's lover. 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] own boy or servant that laid with him". The identity of this boy was Francesco.

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