Born, auspiciously, on April first, 1850, Miss Gwendolyn Caroline Talliferro was the third of three daughters. Her mother, a tiny frail woman who had been ill since the birth of her second child, died within weeks of Gwendolyn's birth. Her sisters, Megan and Eva, were respectively six and three years older than the baby of the family, and Master Talliferro was utterly involved in the running of his small plantation.
Gwendolyn was handed over to the house slaves to be raised, and her first ten years were quite ordinary. Her sisters and she got along well, though her friends tended more to be the black children with whom she was raised. On her own, she would play vividly imagined games of cowboys and indians, switching roles whenever it suited her. She did not learn to read or write beyond her own name, and her mathmatics were left at simple addition and subtraction.
A few months after her tenth birthday, Megan, her oldest sister, was married, to a man little Gwendolyn vehemently disliked. At ten, the youngest Talliferro was beginning to show the promise of beauty, and Robert, the man Megan married, tended to comment on the fact. Gwendolyn, sensibly, didn't trust him a whit. Megan, however, was besotted.
By Gwendolyn's thirteenth birthday, the War had begun. Megan was pregnant with her second child, and in mid-summer, Eva was married to a boy named William. Within weeks of the wedding, William went off to fight, and within weeks after that, was killed.
Eva returned to her father's home, and with quiet determination, wasted away. The new year was ushered in, and with it, Eva died, after confessing to her youngest sister that she couldn't bear to live without William. Gwendolyn was horrified that he could have held so much power over her sister, and began to wonder what she could do to avoid the same sort of fate.
Three weeks later, Megan died giving birth to a son who also died. By Gwendolyn's fourteenth birthday, Robert was petitioning Master Talliferro for Gwendolyn's hand in marriage. At fourteen, Gwendolyn had reached what would be one of her greatest gifts in life: not beautiful, but devestatingly pretty, with enormous blue eyes and long, dark brown hair, she was lovely enough to attract any man's eye without being so unattainably beautiful that women disliked her on sight.
She refused, adamantly, to marry Robert, even on her father's orders. It was entirely too much stress, she claimed, given that both her sisters had died so recently, and, carefully, she hinted that perhaps in a year, she would be enough recovered to wed.
Robert took the bait. He stepped back a little, content to wait another year for the young woman who outshone her dead sister. Gwendolyn, frantically, considered her options. Neither Robert nor her father would accept a delay of greater than a year, and she had no one else to turn to. Her talents as a seamstress, one of the few potential occupations for a woman, were limited, at best, and it was not a field in which she could make enough money to survive on her own.
Sheltered as she was, it was months before Gwendolyn realized the one occupation that might provide her with the cash she would need to survive. Aware, through rumour, of the Underground Railroad, she turned to her old nanny for help. Weeks before her fifteenth birthday, Gwendolyn disappeared.
The end of the Civil War brought her an unexpected and welcomed anonimity: in the turmoil the country saw, it was not quite as unusual as it might have been for a young southern woman to suddenly be without means. She ran to Kansas, and in Topeka, found the madame of the best-reputed whorehouse, gave her name as Caroline Tolliver, and asked to be put to work.
Miss Ruby, a still-striking woman in her late forties, took one look at Miss Caroline and thanked her lucky stars. White, lovely, and young, Ruby got away with charging a dollar a customer for the inexperienced Caroline, and took three quarters of the money herself, making a tidy bundle.
Six months later, Caroline switched houses, taking an astonishing number of regulars with her, charged a dollar fifty per gent, and gave the house fifty percent. Miss Ruby never did forgive herself for letting the enthusiastic young woman slip through her fingers.
That first year, Caroline learned an astonishing amount. She learned what herbs could be taken to prevent pregnancy, and which could be taken to rid herself of a child if it should accidentally come along. She learned that with her looks, she could pick and choose who her customers would be, though she rarely did, not wanting the other girls to dislike her. She learned how to flirt just enough that a gent couldn't help coming back for more, and be willing to pay for it, and, to her utter astonishment, she learned that not all the patrons of whorehouses were men.
In the summer following her sixteenth birthday, Miss Caroline met a man who would, over the next few years, become an integral part of her life. Named John Glenwood, called Gentleman John, he was an aristocratic Southern gentleman, a compulsive gambler and drinker, and the fastest gun Caroline had ever met.
The two were a match from the start. Both handsome, they made a stunning, if ill-reputed, couple, and friendship developed between the whore and the gunslinger. They bantered, at home with each other's choices in life, and in time Gentleman John went from being Caroline's occassional customer to a regular, and then, without discussing it, they simply moved in together, in one of the better rooms of the house Caroline worked at. John was to keep an eye on a scarf on the doorknob to know if Caroline was working, and stay in the saloon below if such was the case.
They continued in this fashion for some three years. Caroline worked steadily, eventually charging a whopping three dollars a customer, a third of which went to the house. Her looks, her enthusiasm, her genuine talent in her chosen profession, and the population base of Topeka allowed her to do this, and Caroline slowly got rich.
She very, very rarely let Gentleman John gamble with her money. It was a risky proposition, of course, and when she did, sometimes it was extremely profitable, and others it was -- less so. On any occasion he might ask her for money, she would simply give it to him without asking anything.
The arrangement worked out admirably until one evening when Gentleman John, having been out on a two-day drunk, forgot to check the scarf when he came home. The fellow he interrupted was far more embarrassed than either Caroline or John was, and determined to give Gentleman John a lesson. He grabbed for his gun, and, hardly thinking about it, John shot him dead and made good his escape.
It failed to occur to John that a whore in a room with a dead man was going to be accused of the murder, no doubt being after the fellow's money. And Caroline did carry a gun. Facing the options of being hanged for murder, sending the authorities after Gentleman John, or running, Caroline collected her cash, her clothing, and once again disappeared.
The next months lead her to Maddock, Montana. A little town with mines nearby, there was more than enough money for Caroline -- now calling herself Gem Trotters -- to decide it was worth settling in and milking for every penny she could get. For four years, she worked at the Dusty Lady Saloon, and her single-handed reputation kept that saloon in excellent business.
In Maddock, Gem found that she could be as outrageous as she wanted: the Ladies Auxillary Committee, dedicated to keeping the town of Maddock pure, well-intentioned and not a Hotbed of Sin, could gossip and be horrified by her, but she and her fellow workers filled a genuine niche in the community, and even the law wouldn't trouble them except for the most grevious transgressions.
Gem had a heyday. Nearly all the heads of the town were her customers at one time or another, and she found enormous delight in flirting with the well-established respectable ladies of the town, most particularly Maggie Kyle, the Sheriff's wife. Maggie, perpetually flabbergasted by the flamboyent whore, staged stratigic retreats whenever possible, which added to Gem's amusement.
She became fast friends with Miguel Mendez, a gorgeous Mexican boy whose talents in bed were legendary, partly thanks to Gem's tales of his exploits. When he married Tess Elliot, a tiny, beautiful Southern belle, Gem was terribly disappointed to lose a customer of his skill, but genuinely delighted for her friend, particularly after Tess, in a somewhat infamous showdown in the restaurant, proved that she was a woman of more backbone than Gem had expected.
She rarely, if ever, made any mention of her wealth, although it was widely granted that Miss Gem Trotters was easily Maddock's top dollar girl. If she showed her money at all, it was in how she dressed: silks or cottons, all carefully tailored for her figure, to show off just enough of the wares to be enticing.
She proved, too, to have a remarkable head for business. Miss Wilona, the owner of the Grey Horse Saloon, offered Gem a position whoring there -- Wilona was convinced that Gem alone was the reason that the Dusty Lady had more business than the Grey Horse. Gritting her teeth, Wilona offered Gem a room at only 25% of her take for the house, and Gem, thoughtfully, counteroffered -- at one third the take going to the house. Wilona, wide-eyed, accepted, and Gem gleefully offered her first night working at the Grey Horse to be half price and everything going to the house. Gaping by now, Wilona accepted that offer, too.
The night changed Gem's life: she managed, after some months of trying, to entice Evan Randolph, one of the more upstanding members of the community and a man Gem admired quite a bit, upstairs. Rather to her horror, over the next months, though she failed to persuade him to join her again, Miss Gem Trotters, Whore Extraordinare, fell in love with Evan. Upon learning he had been conducting a quiet and hopefully permenant relationship with a respectable woman of the town, Gem took it quite well, on the surface.
She followed it by walking back to the Grey Horse, bursting in on Wilona, and collapsing in tears in the woman's lap. Wilona was floored, and Gem, once she'd regained her composure, was extremely embarrassed. She went back to business as usual, still flirting insanely with Evan whenever possible, as much in an attempt to hide her feelings as anything else.
Disasterously, the relationship Evan had been pursuing ended, and he began another one, with a woman easily Gem's equal in both looks and bedroom skills, but with a sterling reputation.