How She Got Her Start:
As a man. Georgina was born George Bertrand. When he began to work as a transsexual prostitute as a young adult, he began going by the name Georgina Beyer (incidentally, "Georgina Beyer" wins our prestigious, "Least Creative Name for a Transvestite Hooker Award").
Whoregina Beyer would have been much more creative.
Georgina quickly fell in with a bad crowd. She started stripping at nightclubs across Sydney, and whoring on the side for extra cash. She soon ended up in the King's Cross neighborhood, a rough area where terrible things tended to happen. Georgina was accosted and raped by four unnamed men.
And while in an action movie, this is the point where Georgina would take to the streets in the name of bloody vengeance, he/she went another direction instead.
What Made Her Great?
After the attack, Georgina left Australia for New Zealand, in one stroke overcoming her trauma and reducing her likelihood of being killed by one of the 14,392 species of poisonous animals that call land down under home. In 1984, Georgina underwent a sex change. She began to work heavily as an actress, and then as a radio host. Finally, in the early 90s, she got into local politics.
She became the world's first transgendered mayor in 1995, a feat which was only eclipsed by her surprise 1999 election to the New Zealand Parliament (a parliament is like congress, but with substantially less cane fighting).
God bless America.
Georgina spent eight terms as the world's first transgendered MP and retired in 2007. She is still an active force in the fight for gay, lesbian, bisexual and transgendered rights worldwide. And if in her spare time she takes to the streets to hunt down her attackers, perhaps with a huge Australian knife up her sleeve... well, that's none of our business.
5th century, AD.
How She Got Her Start:
History remembers Theodora as the wife and co-ruler of the great Justinian, the most lauded ruler of the Eastern Roman Empire. But Theodora wasn't born an Empress.
When her father died, Theodora, her mother and her two sisters were rendered destitute. Desperate for money, Theo's mother sent her three daughters off to work "in the theater." By this point in the list, you know what that means.
Theo took to harlotry like a duck takes to water. She couldn't sing or dance or play an instrument so, to make up for it, she became the most promiscuous courtesan Constantinople had ever seen. The historian, Procopius, said that she "gave her youth to anyone she met, in utter abandonment." Which is basically a fancy way to say she got ridden more than the town bicycle.
The Empress, after retiring from her career in fornication management.
Procopius elaborated on the subject with:
Often she would go picnicking with 10 young men or more, in the flower of their strength and virility, and dallied with them all, the whole night through. When they wearied of the sport, she would approach their servants, perhaps 30 in number, and fight a duel with each of these; and even thus found no allayment of her craving.
Translation: She made love to 10 virile men until they passed out, then she played crotch-soccer with all 30 of their slaves.
Once, visiting the house of an illustrious gentleman, they say she mounted the projecting corner of her dining couch, pulled up the front of her dress, without a blush, and thus carelessly showed her wantonness.
Translation: Real people got tired too easily, so she played pelvic pinochle with the couch instead.
And though she flung wide three gates to the ambassadors of Cupid, she lamented that nature had not similarly unlocked the straits of her bosom, that she might there have contrived a further welcome to his emissaries.
Translation: Three holes just aren't enough.
All of 'em. At the same time. And that fountain, too.
What Made Her Great?
Eventually Theo found a John that she wanted to take home for more than one night. Fortunately for her, that John was the Emperor Justinian. Theodora became his valued co-ruler and was, by all accounts, an equal partner in the ruling of the Empire.
During her years at the top, the scarlet-woman-turned-Empress cracked down on forced prostitution, made rape punishable by death and helped establish basic property rights for women across the Eastern Empire. Despite her lofty status, Theodora never forgot her humble roots. She was considered a friend to the poor, and one of the greatest women's rights reformers in history.
Hmmmm... kind of makes Pretty Woman look like a big pile of vapid bullshit by comparison.
And because we know you can't get enough tales of sex (pervert), check out History's 7 Most Astounding Sexual Resumes and The 6 Raunchiest, Most Depraved Sex Acts (From the Bible).
And visitCracked.com's Sex Picks... sorry, Top Picks.