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A youthful lad cries out as his head is forcefully held, a large digit pressing into his face as his father's mighty palm holds him by the neck. This scene from Abraham's Sacrifice visits the Uffizi Gallery, evoking distress through Caravaggio's chilling portrayal of the suffering youth from the biblical account. It seems as if the patriarch, instructed by God to kill his offspring, could snap his neck with a solitary turn. Yet the father's chosen method involves the silvery grey blade he holds in his other hand, ready to slit the boy's neck. A definite aspect remains – whoever posed as the sacrifice for this breathtaking work displayed extraordinary expressive ability. Within exists not just dread, shock and begging in his shadowed eyes but additionally deep sorrow that a guardian could betray him so completely.

He adopted a well-known biblical tale and made it so vibrant and raw that its terrors seemed to unfold right in front of the viewer

Standing in front of the artwork, observers identify this as a actual countenance, an precise depiction of a adolescent subject, because the same boy – recognizable by his disheveled hair and almost dark eyes – appears in several other works by Caravaggio. In every instance, that highly expressive visage commands the composition. In Youth With a Ram, he peers playfully from the shadows while holding a lamb. In Victorious Cupid, he grins with a hardness learned on the city's streets, his dark plumed wings demonic, a unclothed adolescent running chaos in a well-to-do dwelling.

Victorious Cupid, currently displayed at a British gallery, constitutes one of the most embarrassing artworks ever painted. Viewers feel totally disoriented looking at it. Cupid, whose arrows inspire people with frequently agonizing desire, is portrayed as a extremely real, vividly illuminated nude figure, straddling toppled-over items that comprise musical instruments, a music manuscript, metal armour and an builder's T-square. This heap of possessions echoes, intentionally, the mathematical and construction gear scattered across the floor in Albrecht Dürer's print Melancholy – except here, the melancholic mess is caused by this smirking deity and the mayhem he can release.

"Affection sees not with the vision, but with the soul, / And thus is winged Cupid depicted sightless," wrote the Bard, just prior to this work was produced around 1601. But the painter's god is not unseeing. He gazes directly at the observer. That face – ironic and rosy-faced, looking with brazen assurance as he poses naked – is the identical one that shrieks in terror in Abraham's Test.

When Michelangelo Merisi da Caravaggio created his multiple images of the identical distinctive-looking kid in Rome at the start of the seventeenth century, he was the highly celebrated religious painter in a city ignited by Catholic revival. The Sacrifice of Isaac demonstrates why he was sought to adorn sanctuaries: he could take a scriptural narrative that had been portrayed many occasions previously and render it so new, so raw and physical that the horror seemed to be occurring directly before you.

Yet there was a different aspect to Caravaggio, evident as quickly as he arrived in Rome in the cold season that ended the sixteenth century, as a painter in his early twenties with no mentor or patron in the urban center, just talent and audacity. Most of the paintings with which he captured the holy metropolis's eye were anything but holy. That may be the absolute earliest hangs in the UK's art museum. A young man parts his red lips in a yell of pain: while stretching out his filthy digits for a fruit, he has rather been bitten. Youth Bitten by a Reptile is eroticism amid poverty: observers can discern Caravaggio's dismal room mirrored in the cloudy waters of the transparent vase.

The boy wears a pink flower in his hair – a emblem of the erotic commerce in Renaissance art. Northern Italian painters such as Tiziano and Jacopo Palma depicted prostitutes grasping blooms and, in a painting destroyed in the WWII but known through photographs, Caravaggio portrayed a famous woman prostitute, holding a posy to her chest. The meaning of all these floral signifiers is obvious: sex for purchase.

How are we to interpret of the artist's erotic portrayals of youths – and of one boy in specific? It is a inquiry that has divided his interpreters since he gained mega-fame in the twentieth century. The complicated past reality is that the painter was neither the homosexual icon that, for example, Derek Jarman presented on screen in his 1986 film about the artist, nor so entirely pious that, as some artistic historians improbably assert, his Boy With a Basket of Fruit is in fact a portrait of Christ.

His initial paintings do make explicit sexual implications, or including offers. It's as if the painter, then a penniless youthful artist, aligned with the city's prostitutes, offering himself to live. In the Florentine gallery, with this idea in mind, observers might turn to another early creation, the 1596 masterpiece Bacchus, in which the god of wine gazes coolly at you as he begins to untie the black sash of his robe.

A several years following Bacchus, what could have driven the artist to paint Victorious Cupid for the art patron Vincenzo Giustiniani, when he was finally growing nearly respectable with important ecclesiastical projects? This profane pagan deity resurrects the erotic challenges of his early paintings but in a more intense, uneasy manner. Fifty years later, its hidden meaning seemed clear: it was a portrait of Caravaggio's companion. A English traveller saw Victorious Cupid in about 1649 and was told its figure has "the body & face of [Caravaggio's|his] own boy or assistant that laid with him". The identity of this boy was Cecco.

The painter had been dead for about forty annums when this story was recorded.