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A young lad screams while his head is forcefully held, a large digit pressing into his cheek as his parent's powerful hand holds him by the throat. That moment from The Sacrifice of Isaac visits the Florentine museum, creating unease through Caravaggio's harrowing rendition of the tormented child from the scriptural narrative. It seems as if Abraham, commanded by the Divine to kill his son, could snap his neck with a solitary turn. However the father's preferred method involves the silvery steel knife he grips in his other palm, ready to slit Isaac's neck. One definite element stands out – whoever modeled as the sacrifice for this astonishing work demonstrated extraordinary acting skill. Within exists not only fear, surprise and begging in his shadowed gaze but also deep sorrow that a guardian could abandon him so completely.

The artist took a well-known biblical tale and transformed it so fresh and raw that its horrors seemed to unfold directly in view of you

Standing in front of the artwork, observers recognize this as a real face, an accurate depiction of a adolescent model, because the same boy – recognizable by his disheveled hair and almost black eyes – appears in several additional paintings by Caravaggio. In every case, that highly emotional visage commands the composition. In John the Baptist, he gazes mischievously from the shadows while holding a ram. In Victorious Cupid, he grins with a hardness learned on the city's alleys, his black feathery appendages sinister, a naked child creating riot in a affluent residence.

Victorious Cupid, presently displayed at a London museum, constitutes one of the most discomfiting masterpieces ever created. Viewers feel totally disoriented gazing at it. The god of love, whose arrows inspire people with often agonizing desire, is portrayed as a very tangible, brightly lit nude figure, standing over toppled-over items that comprise stringed devices, a music manuscript, metal armor and an architect's T-square. This pile of possessions resembles, intentionally, the geometric and architectural equipment scattered across the floor in Albrecht Dürer's engraving Melencolia I – except here, the gloomy mess is caused by this smirking deity and the mayhem he can release.

"Affection looks not with the eyes, but with the soul, / And therefore is feathered Cupid painted sightless," penned Shakespeare, just prior to this work was produced around the early 1600s. But the painter'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 same one that shrieks in terror in The Sacrifice of Isaac.

As the Italian master created his multiple images of the same unusual-looking kid in Rome at the dawn of the seventeenth century, he was the highly celebrated sacred painter in a city ignited by religious renewal. Abraham's Offering reveals why he was commissioned to adorn churches: he could adopt a scriptural story that had been depicted numerous times previously and render it so fresh, so raw and visceral that the horror appeared to be occurring immediately in front of you.

However there was another aspect to Caravaggio, evident as quickly as he came in the capital in the cold season that concluded 1592, as a painter in his initial twenties with no teacher or supporter in the urban center, just skill and audacity. Most of the paintings with which he caught the sacred city's attention were everything but devout. That could be the absolute earliest hangs in London's art museum. A young man parts his red mouth in a yell of pain: while reaching out his dirty digits for a fruit, he has rather been bitten. Youth Bitten by a Reptile is eroticism amid poverty: observers can see Caravaggio's gloomy chamber mirrored in the cloudy liquid of the glass vase.

The boy sports a rose-colored flower in his hair – a symbol of the sex commerce in Renaissance art. Northern Italian artists such as Tiziano and Jacopo Palma depicted courtesans holding blooms and, in a painting destroyed in the second world war but documented through photographs, the master represented a renowned woman courtesan, holding a posy to her bosom. The message of all these floral signifiers is clear: sex for purchase.

What are we to interpret of the artist's sensual depictions of boys – and of a particular adolescent in particular? It is a question that has divided his interpreters since he gained widespread recognition in the 1980s. The complex historical truth is that the artist was not the queer icon that, for instance, Derek Jarman presented on film in his twentieth-century movie Caravaggio, nor so entirely devout that, as certain artistic historians improbably assert, his Boy With a Basket of Fruit is actually a likeness of Jesus.

His early paintings indeed offer overt erotic suggestions, or even offers. It's as if Caravaggio, then a penniless young artist, identified with the city's prostitutes, offering himself to survive. In the Uffizi, with this idea in mind, observers might look to another initial creation, the sixteenth-century masterpiece the god of wine, in which the deity of wine gazes calmly at the spectator as he starts to untie the dark ribbon of his robe.

A few years following Bacchus, what could have driven the artist to paint Victorious Cupid for the art patron Vincenzo Giustiniani, when he was finally becoming nearly respectable with prestigious ecclesiastical commissions? This unholy pagan deity resurrects the erotic challenges of his early works but in a more intense, unsettling manner. Fifty years afterwards, its secret seemed obvious: it was a representation of Caravaggio's companion. A British traveller saw Victorious Cupid in about 1649 and was told its figure has "the physique and countenance of [Caravaggio's|his] owne boy or servant that laid with him". The name of this boy was Cecco.

The painter had been deceased for about forty annums when this account was documented.