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A young boy screams as his skull is firmly gripped, a massive thumb pressing into his face as his parent's powerful palm grasps him by the neck. This moment from Abraham's Sacrifice visits the Uffizi Gallery, evoking unease through Caravaggio's harrowing portrayal of the tormented youth from the scriptural narrative. It seems as if Abraham, instructed by God to sacrifice his offspring, could break his neck with a single turn. Yet Abraham's chosen approach involves the silvery steel knife he holds in his other palm, prepared to slit Isaac's throat. A certain element remains – whoever posed as Isaac for this breathtaking piece displayed remarkable expressive skill. There exists not just dread, surprise and pleading in his shadowed gaze but also deep grief that a guardian could betray him so completely.

The artist adopted a familiar scriptural story and made it so vibrant and raw that its horrors seemed to happen directly in view of you

Viewing in front of the artwork, viewers recognize this as a real countenance, an accurate record of a adolescent subject, because the identical boy – recognizable by his tousled locks and almost dark eyes – appears in two additional paintings by the master. In each case, that highly expressive face commands the composition. In Youth With a Ram, he peers mischievously from the darkness while holding a ram. In Victorious Cupid, he grins with a hardness learned on Rome's streets, his black feathery wings demonic, a unclothed adolescent creating chaos in a well-to-do dwelling.

Victorious Cupid, currently exhibited at a British gallery, represents one of the most embarrassing masterpieces ever painted. Viewers feel completely disoriented gazing at it. The god of love, whose arrows inspire people with frequently painful desire, is shown as a very real, brightly lit unclothed figure, straddling overturned objects that include stringed devices, a music score, plate armour and an builder's T-square. This heap of possessions echoes, intentionally, the geometric and architectural gear scattered across the floor in Albrecht Dürer's print Melancholy – save in this case, the melancholic mess is caused by this grinning Cupid and the turmoil he can release.

"Affection sees not with the eyes, but with the mind, / And therefore is feathered Love depicted sightless," penned Shakespeare, shortly prior to this work was produced around the early 1600s. But Caravaggio's god is not blind. He stares directly at the observer. That face – sardonic and ruddy-faced, looking with brazen assurance as he poses unclothed – is the identical one that screams in terror in The Sacrifice of Isaac.

As the Italian master painted his multiple images of the identical unusual-looking kid in the Eternal City at the dawn of the 17th century, he was the most celebrated religious painter in a metropolis ignited by religious renewal. Abraham's Offering reveals why he was commissioned to decorate churches: he could take a scriptural story that had been depicted numerous occasions before and make it so fresh, so unfiltered and physical that the terror seemed to be happening directly in front of the spectator.

Yet there existed another side to the artist, apparent as quickly as he came in the capital in the cold season that concluded the sixteenth century, as a painter in his initial 20s with no mentor or supporter in the urban center, just skill and audacity. Most of the works with which he captured the sacred metropolis's eye were everything but devout. What may be the absolute earliest resides in the UK's National Gallery. A young man parts his red lips in a scream of pain: while reaching out his filthy digits for a fruit, he has rather been attacked. Youth Bitten by a Reptile is eroticism amid poverty: observers can see Caravaggio's gloomy chamber reflected in the cloudy waters of the glass vase.

The adolescent sports a rose-colored blossom in his hair – a symbol of the erotic trade in early modern art. Venetian artists such as Titian and Jacopo Palma portrayed prostitutes holding blooms and, in a work destroyed in the second world war but known through images, the master represented a famous woman courtesan, clutching a posy to her chest. The message of all these floral signifiers is obvious: intimacy for purchase.

How are we to make of the artist's sensual portrayals of boys – and of one adolescent in specific? It is a inquiry that has split his commentators ever since he achieved widespread recognition in the twentieth century. The complicated past reality is that the painter was neither the queer hero that, for example, Derek Jarman put on film in his 1986 film Caravaggio, nor so completely pious that, as certain artistic scholars improbably assert, his Youth Holding Fruit is in fact a likeness of Christ.

His early paintings indeed make overt erotic implications, or even propositions. It's as if Caravaggio, then a penniless youthful creator, aligned with the city's prostitutes, selling himself to live. In the Uffizi, with this thought in consideration, observers might turn to an additional early work, the sixteenth-century masterpiece Bacchus, in which the god of wine gazes calmly at you as he starts to untie the dark sash of his garment.

A few annums after 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 important church commissions? This profane non-Christian god revives the erotic challenges of his initial paintings but in a more powerful, unsettling way. Fifty years afterwards, its hidden meaning seemed clear: it was a representation of Caravaggio's companion. A English traveller viewed Victorious Cupid in about 1649 and was told its subject has "the physique and countenance of [Caravaggio's|his] owne youth or servant that slept with him". The name of this adolescent was Cecco.

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