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The youthful boy screams while his head is firmly gripped, a large digit pressing into his cheek as his father's powerful palm grasps him by the throat. That scene from Abraham's Sacrifice appears in the Florentine museum, evoking unease through Caravaggio's chilling rendition of the tormented child from the biblical account. The painting seems as if Abraham, instructed by the Divine to sacrifice his offspring, could break his spinal column with a solitary turn. Yet the father's preferred method involves the silvery grey blade he holds in his other palm, prepared to cut the boy's throat. A definite aspect remains – whoever posed as the sacrifice for this breathtaking piece demonstrated remarkable expressive ability. Within exists not just dread, shock and begging in his darkened eyes but also profound sorrow that a guardian could betray him so completely.

He adopted a well-known scriptural story and made it so fresh and raw that its horrors seemed to happen directly in view of you

Standing before the artwork, observers recognize this as a real face, an accurate depiction of a young subject, because the identical youth – recognizable by his disheveled hair and almost black pupils – features in two other works by Caravaggio. In every case, that richly expressive visage commands the composition. In Youth With a Ram, he gazes mischievously from the shadows while holding a lamb. In Victorious Cupid, he smirks with a toughness acquired on the city's streets, his dark plumed appendages sinister, a unclothed child running riot in a affluent dwelling.

Victorious Cupid, currently exhibited at a London museum, represents one of the most embarrassing artworks ever created. Viewers feel totally unsettled gazing at it. The god of love, whose darts inspire people with frequently painful longing, is portrayed as a extremely real, brightly lit unclothed figure, standing over overturned objects that comprise musical instruments, a music manuscript, plate armour and an builder's T-square. This pile of items resembles, intentionally, the geometric and construction equipment strewn across the ground in the German master's print Melencolia I – save in this case, the gloomy mess is caused by this grinning deity and the turmoil he can release.

"Love looks not with the vision, but with the soul, / And thus is feathered Cupid painted sightless," wrote Shakespeare, shortly prior to this work was produced around the early 1600s. But Caravaggio's god is not unseeing. He gazes straight at you. That countenance – ironic and rosy-faced, looking with bold assurance as he struts naked – is the identical one that screams in terror in Abraham's Test.

When the Italian master created his multiple portrayals of the same unusual-looking kid in Rome at the start of the seventeenth century, he was the highly acclaimed sacred painter in a city ignited by Catholic revival. The Sacrifice of Isaac demonstrates why he was sought to adorn churches: he could adopt a biblical narrative that had been depicted numerous occasions before and make it so new, so raw and physical that the horror seemed to be occurring immediately before you.

Yet there was a different side to Caravaggio, apparent as soon as he came in Rome in the cold season that concluded the sixteenth century, as a painter in his initial 20s with no mentor or patron in the urban center, only talent and audacity. The majority of the paintings with which he caught the holy metropolis's eye were everything but holy. That may be the absolute earliest resides in the UK's art museum. A youth parts his red lips in a yell of pain: while reaching out his dirty digits for a fruit, he has instead been attacked. Youth Bitten by a Reptile is sensuality amid poverty: viewers can discern Caravaggio's dismal chamber mirrored in the cloudy liquid of the transparent container.

The adolescent wears a pink flower in his coiffure – a emblem of the erotic trade in Renaissance art. Venetian artists such as Titian and Jacopo Palma portrayed prostitutes grasping flowers and, in a work destroyed in the second world war but documented through images, the master represented a famous woman courtesan, clutching a posy to her chest. The meaning of all these botanical indicators is clear: sex for purchase.

How are we to make of Caravaggio's erotic depictions of boys – and of one adolescent in specific? It is a question that has split his interpreters ever since he gained mega-fame in the twentieth century. The complicated past reality is that the artist was neither the homosexual icon that, for example, Derek Jarman put on film in his twentieth-century movie about the artist, nor so completely pious that, as some artistic historians unbelievably assert, his Youth Holding Fruit is in fact a portrait of Christ.

His initial works indeed make overt erotic suggestions, or including offers. It's as if Caravaggio, then a destitute youthful artist, identified with Rome's sex workers, selling himself to live. In the Uffizi, with this thought in consideration, observers might turn to an additional initial work, the sixteenth-century masterpiece the god of wine, in which the deity of alcohol stares coolly at you as he starts to untie the black ribbon of his robe.

A several years after the wine deity, what could have motivated Caravaggio to create Victorious Cupid for the art collector Vincenzo Giustiniani, when he was at last becoming almost established with important church projects? This unholy pagan god resurrects the erotic provocations of his initial works but in a increasingly powerful, unsettling way. Half a century later, its secret seemed obvious: it was a representation of Caravaggio's lover. A English visitor 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 boy was Cecco.

The painter had been deceased for about 40 annums when this story was recorded.