Orlando was born in Thebes of 1260 BC as Bio, daughter of the blind seer Tiresias, once cursed to transform into a woman for seven years. Tiresias had passed his gift of prophecy to his older daughter Manto, who would go on to be an Oracle of Delphi, while Bio inherited his omnisexuality that manifested itself at the age of ten when she transformed into a boy. Out of shame, Tiresias sold his son to pirate slavers bound for Egypt, where he became a favorite of Ramesses II.
Nine years later, having aged beyond the pharaoh's tastes, Orlando joined an expedition bound for the horn of Africa, where as soon as they docked, he transformed back into a woman. Fearing what might become of her among her crewmates, she fled into the jungle and wandered for weeks, eventually stumbling into the city of Kor in Uganda, where she found a mystical pool of lapid, liquid flame in which she bathed and emerged an Immortal.
After spending several decades in a community of immortals who had bathed in the pool of flame, Bion, as he would be known as a man, went to defend Troy. It was there that he met Aeneas, who he would join in for eighty years, eventually leaving with his great-grandson, Brutus, to travel at the behest of the goddess Diana to a northern isle where he would found a mighty nation. Bion, Brutus and their companions would spend a decade culling the land they called Brutain's population, which consisted of a grotesque race of giants.
As a Woman
Bored and a female once again, Bio traveled the world, becoming a handmaiden of King Mu of China, as well as a lover to the Immortal Royal Mother of the West. Renamed Vita as a woman and Vito as a man, becoming a lover of Remus and later Romulus,after being seduced, fight for Persia in Marathon, assist Alexander of Macedonia, read the entire contents of the Library of Alexandria, take part in Spartacus' slave revolt and fight for Julius Caesar and later for Marc Antony.
She eventually returned to myth-soaked Britain, where she was seduced by Ambrosious Merlinus. As the years passed, Vita witnessed the founding of King Uthar’s kingdom as well as his son Arthur's succession and as Vito fought alongside the Knights of the Round table in the battle of Camlann, where he salvaged Excalibur and rechristened it Durendal. Vito abandoned Britain again, travelling to witness Beowulf defeating Grendel, Siegfried vanquishing Fafner and even beheld Ragnarok in an alternate dimension.
As a Man
Now using the name Roland, he joined the knights of Charlemagne and fought the Saracens in Pyrenees until he was the last man standing. Admiring his fortitude, the Saracens spared him and invited him to join them, and Orlando accepted. In Baghdad he would come to be known as Orlando, and became acquainted with Caliph Harum al-Rashid, his consort Scheherazade and most importantly, Sinbad, who would become his most enduring love, until he eventually left for an Eight Voyage from which he would never return. Orlando then fought in the Crusades, became an assistant to William Tell as well as one of the Merry Men, posed for the Mona Lisa and eventually came to be Johann Faust's assistant, through whom he met a young Prospero, who had come to learn of magic.
Orlando would escort the magician in the years to come, and was at his side when he visited Queen Gloriana who commanded them to form a group of adventurers that would later become the first iteration of the League of Extraordinary Gentlemen. Sometime later, with many of the League departing with Prospero into the Blazing World, as well as King Jacob's purge of the faeries, Orlando traveled the world once again, returning to join the next iteration of the League, this time led by Lemuel Gulliver. Orlando would become a companion and lover of fellow members, Fanny Hill, Percy and Marguerite Blakeney, until Gulliver's demise of old age.
League of Extraordinary Gentlemen
Orlando then headed to the orient, reaching Shangri-La where years later was found by Allan Quatermain and Mina Murray, who had come to recruit her to the fourth iteration of the League. In the years that followed, he'd become involved with Allan and Mina in a polyamorous relationship, and as part of the league along A.J. Raffles and Thomas Carnacki, investigated a circle of magicians based at King's Court known as the Profess-House, where he survived an assault by the circle's leader, Oliver Haddo. He also helped repel a pirate raid on East London and averted some sort of disaster at King George's coronation. In 1913, when the league battled their French counterparts as part of a ploy orchestrated by their German equivalent, he fought Monsieur Zenith atop the Paris Opera House until explosives buried under the building detonated, ending their bout indecisively.
With the outbreak of World War I, Raffles and Orlando both enlisted in the British Army. At the battle of Mons, he alongside Captain Edmund Blackadder, witnessed the Phantom Bowmen of Agincourt aiding the British. Orlando next spent the twenties as one of the Bright Young People set. Sometime in the late twenties, he, alongside Carnacki, Mina and Allan battled the great old ones at Brinkley Court who had possessed the bodies of Dahlia Travers and her companions.
With the outbreak of World War II, Orlando enlisted in the Royal Air Force, and fought alongside aces such as Bigglesworth, Hobblethwaite, and G-8. After being shot shown over France and escaping to London, he found his teammates missing. He took the time to write his memoirs, and disappeared sometime in 1944, having been turned into an orange cat through sorcery. Having reverted back to human form and relocated to the Blazing World, she was reunited with Allan and Mina in 1958.
Orlando is last seen with Allan in Paris of 1964 where she, known simply as O engages with him and the descendants of the Silling Castle survivors in sexual games of dominance and submission. Mina does not accompany them, and it is hinted that she had began drifting apart from both Orlando and Allan.
In the year 1969, Mina forms a League with the surviving members of the Second Murray Group in the hopes of preventing the birth of the Moonchild whom is destined to bring forth a dreadful new eon. Orlando is rather dismisses much of Mina's attempts to adapt to the times and the entire era as being hollow in their peace objectives. Orlando aides in killing Soror Julia. Allan and Orlando search for Mina in Hyde Park but cannot find her.
In 1977 female again and dying her hair blonde and sporting a mowhawk she angrily leaves Allan who has succumbed to his drug problems once more.
Forty years later he is found in 2009 fighting with the British Army under Colonel Cuckoo in Qu'mar, fighting ironically Operation Sindbad.