Roggerio was the son of Lysandro Rogare. He had five trueborn brothers, Lysaro, Moredo, Lotho, Drako, and Fredo, and three trueborn sisters, Larra, Lysara, and Marra, as well as sixteen bastard siblings.
When his sister Larra came to King's Landing as the wife of Prince Viserys Targaryen, Roggerio, Moredo, and Lotho came with her. Roggerio and Lotho were fluent in the common tongue, although Moredo was not.
Roggerio opened a high-class pleasure house which he called the Mermaid near the River Gate in the capital. The Mermaid was no common brothel, but an opulent establishment, full of exotic animals such as parrots and monkeys. Its prostitutes were exotic too, from every corner of the world and cost ten times more than common whores. Despite this Roggerio never lacked for customers, mainly high lords, knights and rich merchants. Roggerio banned Tessario the Tiger from the Mermaid when the sellsword struck one of his girls.
In 135 AC Roggerio was arrested at the Mermaid by Ser Marston Waters when House Rogare was accused of treason. Although the treason against King Aegon III Targaryen was later proven unfounded, the new Hand of the King, Lord Torrhen Manderly still sentenced Roggerio to seven lashes, when Roggerio asked "for what?", Lord Manderly replied "for being a thrice damned Lyseni".
After his punishment and release, he sold his brothel and everything in it to purchase a great cog which he named the Mermaid's Daughter, which effectively was the pillowhouse reborn with sails. Roggerio departed King's Landing and sailed the sea, trading in wines and carnal pleasures at every port he visited.