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A youthful boy cries out as his head is forcefully gripped, a massive digit digging into his face as his parent's mighty hand holds him by the throat. That moment from The Sacrifice of Isaac appears in the Florentine museum, creating unease through Caravaggio's harrowing portrayal of the tormented child from the scriptural narrative. The painting seems as if the patriarch, commanded by God to sacrifice his son, could snap his spinal column with a single turn. However Abraham's chosen method involves the silvery grey blade he holds in his other palm, prepared to cut Isaac's neck. A definite element remains – whomever modeled as the sacrifice for this astonishing work displayed remarkable acting skill. There exists not only dread, surprise and begging in his shadowed gaze but also deep grief that a protector could abandon him so completely.

He adopted a familiar scriptural tale and transformed it so vibrant and visceral that its horrors seemed to unfold directly in view of the viewer

Standing in front of the artwork, viewers recognize this as a real countenance, an accurate record of a adolescent subject, because the same boy – recognizable by his tousled hair and nearly black pupils – features in several additional paintings by the master. In every instance, that highly expressive visage commands the composition. In John the Baptist, he peers mischievously from the shadows while holding a ram. In Amor Vincit Omnia, he grins with a hardness learned on Rome's alleys, his dark feathery appendages sinister, a naked child running riot in a affluent dwelling.

Amor Vincit Omnia, currently displayed at a London gallery, constitutes one of the most embarrassing artworks ever painted. Viewers feel completely disoriented looking at it. Cupid, whose darts inspire people with frequently agonizing longing, is shown as a very real, vividly lit nude form, straddling toppled-over objects that comprise musical devices, a musical score, plate armor and an builder's T-square. This heap of possessions resembles, intentionally, the mathematical and construction equipment strewn across the floor in Albrecht Dürer's engraving Melancholy – save in this case, the gloomy mess is caused by this smirking Cupid and the mayhem he can release.

"Affection looks not with the eyes, but with the soul, / And thus is winged Love depicted sightless," wrote Shakespeare, shortly before this painting was produced around 1601. But Caravaggio's Cupid is not unseeing. He gazes straight at the observer. That face – ironic and rosy-cheeked, looking with brazen assurance as he struts naked – is the same one that screams in terror in Abraham's Test.

When Michelangelo Merisi da Caravaggio created his three portrayals of the identical unusual-looking youth in the Eternal City at the dawn of the seventeenth century, he was the most acclaimed sacred artist in a metropolis ignited by religious revival. Abraham's Offering demonstrates why he was sought to decorate sanctuaries: he could take a biblical story that had been depicted numerous times before and render it so fresh, so raw and visceral that the terror appeared to be occurring directly in front of the spectator.

Yet there existed another aspect to Caravaggio, evident as soon as he came in the capital in the cold season that ended the sixteenth century, as a painter in his early twenties with no mentor or patron in the urban center, just skill and boldness. Most of the works with which he captured the sacred metropolis's eye were everything but holy. That could be the very first hangs in London's art museum. A youth parts his red mouth in a yell of agony: while reaching out his dirty fingers for a cherry, he has rather been bitten. Youth Bitten by a Reptile is sensuality amid poverty: viewers can discern Caravaggio's gloomy chamber mirrored in the murky waters of the transparent vase.

The boy sports a rose-colored flower in his hair – a symbol of the erotic trade in Renaissance art. Northern Italian artists such as Tiziano and Palma Vecchio depicted courtesans holding flowers and, in a work destroyed in the second world war but known through images, the master portrayed a renowned woman prostitute, clutching a posy to her chest. The meaning of all these floral indicators is clear: sex for sale.

How are we to make of the artist's sensual portrayals of youths – and of a particular adolescent in specific? It is a inquiry that has divided his interpreters ever since he gained widespread recognition in the twentieth century. The complicated historical reality is that the painter was neither the homosexual icon that, for instance, Derek Jarman presented on screen in his twentieth-century film Caravaggio, nor so entirely pious that, as some art historians unbelievably claim, his Youth Holding Fruit is actually a likeness of Christ.

His early paintings do offer overt erotic suggestions, or including propositions. It's as if the painter, then a destitute youthful artist, identified with the city's prostitutes, offering himself to live. In the Florentine gallery, with this thought in consideration, viewers might look to another early work, the 1596 masterpiece the god of wine, in which the deity of alcohol gazes calmly at the spectator as he starts to untie the black sash of his robe.

A several years following the wine deity, what could have driven Caravaggio to paint Amor Vincit Omnia for the artistic collector Vincenzo Giustiniani, when he was finally growing almost established with important church commissions? This profane non-Christian god revives the erotic challenges of his early paintings but in a increasingly intense, unsettling way. Half a century later, its secret seemed clear: it was a portrait of the painter's companion. A British traveller viewed Victorious Cupid in about the mid-seventeenth century and was informed its subject has "the physique and countenance of [Caravaggio's|his] own youth or assistant that slept with him". The name of this boy was Francesco.

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