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A young lad cries out while his skull is firmly held, a large thumb pressing into his face as his father's powerful hand grasps him by the throat. This scene from The Sacrifice of Isaac visits the Uffizi Gallery, evoking distress through Caravaggio's harrowing portrayal of the tormented youth from the biblical account. The painting appears as if the patriarch, commanded by God to sacrifice his son, could break his spinal column with a single twist. However Abraham's chosen approach involves the silvery steel knife he holds in his remaining hand, ready to slit Isaac's neck. A certain aspect stands out – whoever posed as Isaac for this breathtaking work demonstrated extraordinary acting skill. There exists not just fear, shock and pleading in his darkened eyes but also profound grief that a protector could betray him so utterly.

He adopted a well-known scriptural tale and made it so vibrant and visceral that its terrors seemed to happen directly in view of the viewer

Standing in front of the painting, observers recognize this as a real face, an accurate record of a young subject, because the identical youth – recognizable by his disheveled hair and nearly dark eyes – appears in several other paintings by Caravaggio. In every instance, that richly emotional visage dominates the scene. In Youth With a Ram, he gazes mischievously from the darkness while holding a lamb. In Amor Vincit Omnia, he grins with a toughness learned on the city's alleys, his black feathery appendages sinister, a naked adolescent running riot in a well-to-do residence.

Victorious Cupid, currently exhibited at a British museum, constitutes one of the most discomfiting artworks ever created. Observers feel totally unsettled gazing at it. Cupid, whose darts fill people with frequently painful longing, is shown as a extremely real, brightly lit nude form, straddling toppled-over items that include musical instruments, a musical score, metal armour and an builder's T-square. This heap of possessions echoes, deliberately, the mathematical and construction gear strewn across the floor in the German master's engraving Melencolia I – except here, the gloomy mess is caused by this smirking deity and the turmoil he can release.

"Affection looks not with the eyes, but with the soul, / And thus is feathered Love painted sightless," penned Shakespeare, shortly before this painting was created around the early 1600s. But Caravaggio's Cupid is not blind. He stares directly at the observer. That face – sardonic and rosy-cheeked, staring with bold assurance as he struts unclothed – is the identical one that screams in terror in Abraham's Test.

As Michelangelo Merisi da Caravaggio created his three portrayals of the identical unusual-appearing youth in the Eternal City at the start of the seventeenth century, he was the most celebrated sacred artist in a city enflamed by religious revival. Abraham's Offering reveals why he was commissioned to decorate sanctuaries: he could take a biblical narrative that had been depicted numerous times previously and make it so new, so unfiltered and visceral that the terror appeared to be occurring directly before the spectator.

However there was another aspect to the artist, evident as soon as he came in the capital in the cold season that concluded the sixteenth century, as a artist in his initial twenties with no mentor or patron in the urban center, only talent and audacity. The majority of the works with which he caught the sacred metropolis's attention were everything but devout. That could be the very first hangs in London's National Gallery. A youth parts his red lips in a yell of pain: while reaching out his dirty fingers for a cherry, he has rather been bitten. Youth Bitten by a Reptile is eroticism amid poverty: observers can discern the painter's dismal chamber reflected in the murky waters of the transparent vase.

The adolescent sports a rose-colored flower in his coiffure – a symbol of the erotic trade in Renaissance painting. Venetian painters such as Tiziano and Palma Vecchio portrayed prostitutes holding blooms and, in a painting lost in the second world war but known through photographs, the master represented a renowned woman courtesan, clutching a bouquet to her chest. The meaning of all these botanical indicators is obvious: sex for sale.

What are we to make of Caravaggio's erotic portrayals of boys – and of a particular adolescent in specific? It is a question that has split his commentators ever since he achieved widespread recognition in the 1980s. The complicated past reality is that the painter was neither the queer icon that, for example, the filmmaker put on screen in his twentieth-century movie Caravaggio, nor so completely devout that, as some artistic scholars unbelievably claim, his Boy With a Basket of Fruit is in fact a likeness of Christ.

His early works do make explicit erotic suggestions, or including offers. It's as if Caravaggio, then a penniless young creator, aligned with Rome's sex workers, selling himself to live. In the Uffizi, with this idea in consideration, observers might turn to an additional initial creation, the sixteenth-century masterpiece the god of wine, in which the god of wine stares calmly at the spectator as he begins to undo the black ribbon of his garment.

A few annums following Bacchus, what could have driven Caravaggio to create Victorious Cupid for the art collector Vincenzo Giustiniani, when he was at last becoming nearly established with prestigious church commissions? This profane pagan deity revives the erotic provocations of his early works but in a more intense, unsettling way. Fifty years afterwards, its secret seemed obvious: it was a portrait of Caravaggio's lover. A British traveller saw Victorious Cupid in about the mid-seventeenth century and was told its figure has "the body & face of [Caravaggio's|his] owne boy or assistant that laid with him". The identity of this adolescent was Cecco.

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