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The youthful lad screams while his head is forcefully held, a large digit pressing into his cheek as his father's powerful palm holds him by the throat. That scene from The Sacrifice of Isaac visits the Florentine museum, creating distress through the artist's harrowing rendition of the tormented child from the scriptural account. It seems as if the patriarch, instructed by God to sacrifice his offspring, could break his spinal column with a solitary twist. However the father's chosen approach involves the metallic grey knife he grips in his remaining hand, ready to cut Isaac's throat. One definite aspect stands out – whomever posed as the sacrifice for this breathtaking work demonstrated extraordinary acting skill. There exists not just dread, surprise and begging in his shadowed gaze but also profound grief that a guardian could abandon him so utterly.

The artist took a familiar scriptural story and transformed it so fresh and visceral that its horrors appeared to unfold directly in view of the viewer

Viewing in front of the painting, viewers recognize this as a actual face, an accurate depiction of a young model, because the same boy – recognizable by his tousled hair and nearly black eyes – features in several other works by the master. In every instance, that highly expressive visage commands the scene. In John the Baptist, he gazes playfully from the darkness while holding a ram. In Amor Vincit Omnia, he grins with a toughness learned on the city's streets, his dark feathery wings sinister, a unclothed child running chaos in a affluent residence.

Victorious Cupid, presently exhibited at a London museum, represents one of the most embarrassing artworks ever painted. Observers feel completely disoriented looking at it. The god of love, whose darts fill people with frequently painful desire, is portrayed as a extremely real, brightly illuminated unclothed figure, standing over toppled-over items that include musical instruments, a musical score, metal armor and an architect's ruler. This heap of possessions resembles, deliberately, the mathematical and construction gear scattered across the floor in the German master's print Melancholy – save here, the melancholic disorder is created by this smirking Cupid and the turmoil he can unleash.

"Love sees not with the eyes, but with the mind, / And therefore is winged Love depicted blind," penned the Bard, shortly prior to this work was created around the early 1600s. But the painter's Cupid is not blind. He gazes directly at you. That face – sardonic and ruddy-cheeked, staring with bold confidence as he struts unclothed – is the same one that shrieks in terror in The Sacrifice of Isaac.

When the Italian master painted his three portrayals of the identical unusual-looking kid in Rome at the dawn of the 17th century, he was the highly acclaimed sacred painter in a metropolis enflamed by religious renewal. The Sacrifice of Isaac demonstrates why he was commissioned to decorate sanctuaries: he could adopt a scriptural narrative that had been depicted many times previously and make it so fresh, so raw and visceral that the horror appeared to be happening directly in front of the spectator.

Yet there was another side to the artist, apparent as soon as he arrived in Rome in the cold season that ended the sixteenth century, as a artist in his early twenties with no mentor or supporter in the city, just talent and boldness. The majority of the works with which he caught the sacred city's attention were everything but holy. That may be the absolute first hangs in the UK's National Gallery. A youth parts his crimson lips in a yell of pain: while reaching out his dirty fingers for a cherry, he has instead been bitten. Boy Bitten By a Lizard is sensuality amid poverty: observers can see the painter's gloomy room mirrored in the cloudy waters of the glass container.

The adolescent wears a pink blossom in his coiffure – a emblem of the sex commerce in early modern painting. Venetian artists such as Titian and Jacopo Palma portrayed prostitutes holding blooms and, in a work destroyed in the WWII but documented through images, Caravaggio portrayed a famous female courtesan, clutching a bouquet to her chest. The message of all these floral signifiers is clear: intimacy for purchase.

How are we to interpret of Caravaggio's sensual portrayals of boys – and of a particular adolescent in specific? It is a inquiry that has split his commentators since he achieved mega-fame in the twentieth century. The complicated past truth is that the artist was not the homosexual hero that, for example, Derek Jarman put on screen in his 1986 film Caravaggio, nor so completely pious that, as certain artistic scholars unbelievably assert, his Boy With a Basket of Fruit is actually a portrait of Christ.

His initial works do offer explicit sexual suggestions, or including propositions. It's as if Caravaggio, then a penniless young creator, aligned with Rome's sex workers, offering himself to survive. In the Uffizi, with this idea in mind, observers might look to another early work, the 1596 masterpiece Bacchus, in which the deity of wine gazes calmly at you as he starts to untie the black ribbon of his robe.

A few years following the wine deity, what could have motivated the artist to paint Victorious Cupid for the artistic collector the nobleman, when he was finally becoming almost established with important ecclesiastical projects? This unholy non-Christian god resurrects the erotic challenges of his initial works but in a increasingly powerful, unsettling way. Half a century afterwards, its hidden meaning seemed obvious: it was a portrait of Caravaggio's companion. A English visitor viewed the painting in about 1649 and was informed its figure has "the body & face of [Caravaggio's|his] owne boy or servant that laid with him". The name of this adolescent was Francesco.

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