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The youthful boy screams as his head is firmly held, a massive digit digging into his cheek as his father's mighty palm grasps him by the throat. That scene from Abraham's Sacrifice appears in the Uffizi Gallery, creating unease through the artist's chilling portrayal of the suffering youth from the scriptural account. The painting appears as if Abraham, commanded by the Divine to kill his offspring, could snap his spinal column with a single turn. However the father's preferred approach involves the silvery grey blade he holds in his other palm, ready to cut the boy's throat. One definite aspect remains – whoever posed as the sacrifice for this astonishing piece displayed extraordinary expressive ability. Within exists not only fear, surprise and begging in his darkened gaze but additionally profound grief that a guardian could betray him so completely.

He took a well-known scriptural story and made it so fresh and raw that its terrors seemed to unfold right in front of the viewer

Standing in front of the painting, viewers identify this as a real face, an precise record of a adolescent model, because the identical boy – recognizable by his disheveled locks and nearly black eyes – features in several additional paintings by the master. In each case, that richly emotional face dominates the composition. In Youth With a Ram, he gazes mischievously from the shadows while holding a lamb. In Victorious Cupid, he smirks with a hardness learned on Rome's alleys, his dark plumed wings sinister, a unclothed adolescent creating riot in a affluent dwelling.

Amor Vincit Omnia, presently displayed at a London gallery, constitutes one of the most embarrassing masterpieces ever created. Observers feel totally unsettled gazing at it. The god of love, whose arrows inspire people with frequently agonizing longing, is portrayed as a very real, brightly lit nude figure, straddling overturned items that comprise stringed instruments, a music score, metal armor and an architect's T-square. This heap of possessions echoes, intentionally, the mathematical and architectural equipment strewn across the ground in the German master's engraving Melancholy – save here, the gloomy disorder is caused by this grinning Cupid and the mayhem he can unleash.

"Affection looks not with the eyes, but with the mind, / And thus is winged Cupid depicted blind," wrote Shakespeare, just prior to this work was produced around the early 1600s. But the painter's god is not unseeing. He stares straight at the observer. That face – sardonic and rosy-faced, looking with bold assurance as he struts naked – is the same one that screams in terror in The Sacrifice of Isaac.

When Michelangelo Merisi da Caravaggio painted his three portrayals of the identical unusual-looking youth in the Eternal City at the start of the seventeenth century, he was the most acclaimed religious painter in a city ignited by religious renewal. Abraham's Offering reveals why he was commissioned to decorate sanctuaries: he could take a biblical story that had been portrayed numerous times before and make it so new, so raw and visceral that the horror seemed to be occurring immediately in front of you.

Yet there was another side to the artist, evident as quickly as he arrived in Rome in the winter that concluded 1592, as a painter in his early twenties with no teacher or patron in the urban center, only talent and audacity. Most of the paintings with which he captured the sacred metropolis's eye were anything but holy. That could be the absolute earliest resides in the UK's National Gallery. A youth parts his red mouth in a yell of agony: while stretching out his filthy digits for a fruit, he has rather been attacked. Youth Bitten by a Reptile is eroticism amid squalor: viewers can see Caravaggio's dismal chamber reflected in the cloudy waters of the glass container.

The boy sports a pink flower in his hair – a emblem of the erotic trade in Renaissance art. Northern Italian artists such as Titian and Palma Vecchio portrayed courtesans grasping flowers and, in a painting lost in the second world war but documented through photographs, Caravaggio represented a renowned female courtesan, holding a posy to her chest. The meaning of all these floral indicators is clear: intimacy for purchase.

What are we to interpret of the artist's sensual portrayals of youths – and of one boy in specific? It is a question that has divided his interpreters since he gained mega-fame in the 1980s. The complicated past truth is that the painter was neither the homosexual icon that, for example, Derek Jarman presented on film in his twentieth-century film about the artist, nor so entirely pious that, as some artistic scholars unbelievably claim, his Youth Holding Fruit is actually a portrait of Christ.

His early works indeed offer explicit erotic suggestions, or even propositions. It's as if Caravaggio, then a penniless youthful creator, aligned with Rome's sex workers, selling himself to live. In the Florentine gallery, with this idea in consideration, observers might look to another initial work, the sixteenth-century masterwork the god of wine, in which the deity of wine stares coolly at you as he starts to undo the black ribbon of his robe.

A few annums following the wine deity, what could have driven Caravaggio to paint Victorious Cupid for the artistic patron the nobleman, when he was finally growing almost established with important ecclesiastical projects? This unholy pagan god resurrects the erotic challenges of his initial paintings but in a increasingly intense, unsettling way. Half a century later, its secret seemed clear: it was a representation of the painter's companion. A English traveller viewed the painting in about the mid-seventeenth century and was informed its figure has "the physique and countenance of [Caravaggio's|his] own youth or assistant that laid with him". The identity of this boy was Cecco.

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