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The youthful lad cries out while his head is firmly gripped, a large thumb digging into his cheek as his parent's mighty palm grasps him by the neck. This moment from The Sacrifice of Isaac visits the Uffizi Gallery, creating unease through the artist's chilling rendition of the suffering youth from the biblical narrative. The painting appears as if the patriarch, commanded by God to sacrifice his offspring, could snap his spinal column with a solitary twist. Yet the father's chosen approach involves the metallic grey knife he holds in his remaining palm, ready to slit Isaac's neck. One definite aspect stands out – whoever posed as the sacrifice for this breathtaking piece displayed remarkable expressive ability. Within exists not only fear, shock and pleading in his shadowed eyes but also profound grief that a guardian could betray him so completely.

He took a familiar biblical tale and transformed it so vibrant and visceral that its horrors appeared to happen directly in view of the viewer

Standing before the painting, observers identify this as a real countenance, an precise depiction of a adolescent subject, because the identical youth – identifiable by his disheveled locks and almost dark eyes – appears in two other works by the master. In every instance, that highly expressive visage dominates the scene. In Youth With a Ram, he gazes playfully from the shadows while embracing a ram. In Victorious Cupid, he smirks with a hardness acquired on the city's alleys, his black feathery appendages demonic, a unclothed adolescent creating riot in a affluent dwelling.

Victorious Cupid, presently exhibited at a London museum, constitutes one of the most discomfiting masterpieces ever created. Observers feel totally unsettled gazing at it. The god of love, whose arrows inspire people with frequently painful desire, is shown as a extremely tangible, brightly illuminated unclothed figure, straddling toppled-over items that include musical instruments, a musical manuscript, metal armour and an builder's T-square. This pile of items echoes, intentionally, the mathematical and construction equipment scattered across the ground in the German master's engraving Melencolia I – except in this case, the gloomy mess is caused by this grinning deity and the turmoil he can unleash.

"Love looks not with the eyes, but with the mind, / And therefore is feathered Cupid painted blind," wrote Shakespeare, just before this painting was created around the early 1600s. But the painter's god is not unseeing. He stares directly at the observer. That face – sardonic and ruddy-faced, staring with brazen assurance as he struts naked – is the identical one that screams in terror in Abraham's Test.

As the Italian master painted his three images of the identical distinctive-appearing kid in the Eternal City at the dawn of the seventeenth century, he was the most acclaimed religious artist in a city ignited by religious revival. Abraham's Offering reveals why he was sought to adorn churches: he could adopt a scriptural narrative that had been portrayed many times before and make it so new, so raw and visceral that the horror seemed to be happening immediately in front of the spectator.

Yet there was another aspect to the artist, evident as soon as he came in the capital in the winter that ended the sixteenth century, as a artist in his initial twenties with no mentor or patron in the city, just skill and audacity. The majority of the paintings with which he caught the holy metropolis's attention were anything but holy. That could be the absolute first resides in the UK's National Gallery. A youth opens his red lips in a scream of pain: while stretching out his dirty fingers for a fruit, he has rather been bitten. Youth Bitten by a Reptile is sensuality amid poverty: observers can see the painter's gloomy chamber mirrored in the murky waters of the transparent container.

The adolescent sports a rose-colored blossom in his hair – a emblem of the erotic commerce in early modern art. Venetian artists such as Titian and Palma Vecchio portrayed prostitutes grasping blooms and, in a painting destroyed in the second world war but documented through photographs, the master represented a famous woman prostitute, holding a posy to her bosom. The message of all these botanical indicators is obvious: sex for purchase.

What are we to make of Caravaggio's sensual portrayals of youths – and of a particular adolescent in specific? It is a question that has split his commentators since he achieved mega-fame in the twentieth century. The complex past truth is that the painter was not the queer icon that, for example, the filmmaker presented on screen in his twentieth-century film Caravaggio, nor so entirely pious that, as certain art historians improbably claim, his Boy With a Basket of Fruit is in fact a portrait of Christ.

His initial paintings indeed offer explicit sexual implications, or even offers. It's as if Caravaggio, then a destitute young artist, aligned with Rome's sex workers, offering himself to live. In the Florentine gallery, with this thought in consideration, observers might look to another initial work, the sixteenth-century masterpiece the god of wine, in which the god of alcohol gazes calmly at the spectator as he starts to undo the black sash of his garment.

A several annums following Bacchus, what could have driven Caravaggio to create Victorious Cupid for the artistic patron Vincenzo Giustiniani, when he was at last becoming almost established with important ecclesiastical commissions? This unholy non-Christian god resurrects the sexual provocations of his early works but in a increasingly powerful, uneasy manner. Fifty years later, its secret seemed clear: it was a representation of Caravaggio's lover. A British visitor saw the painting in about 1649 and was informed its figure has "the physique and countenance of [Caravaggio's|his] own youth or servant that laid with him". The identity of this boy was Francesco.

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