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Upon completion of the very first medical examination Joshua Smiles, in a burst of volubility not to be repeated outside of his prayers, explained the rules to be followed during the voyage. He then launched into a lengthy dissertation which included much comment about the dangers of immoral behaviour, the need for cleanliness and the benefits and rewards of a religious life. He left until last his admonition that profanity and blasphemy would earn the harshest of punishments and warned any female prisoner to bring the name of the Almighty God upon her lips in no other manner but in prayerfulness.

Mary and her intake were divided into two groups, each of which was termed a mess. From each mess a monitor was chosen to speak for all. Mary was elected monitor by the insistence of all in her group. Ann Gower was also selected as monitor in the second mess, which contained six convicts who were from Dublin, they being whores and thus thought to be most compatible to the other members.

The prison uniform consisted of a coarse particoloured cotton shift, two petticoats and two sets of ill-fitting undergarments, a pinny, with a spare, and two mob caps. The women's own clothes were washed by three members of each mess, hung out on the deck to dry then dry packed away in boxes with camphor balls. The idea behind imposing uniformity of dress was to eliminate a natural pecking order derived from the status of possessions – rags or fine gowns, tortoise shell brushes or combs of ox bone, bottles of perfumes or tincture of lavender water, a fine brooch or merely a few bright buttons or a single trinket. These were all placed on the mess inventory and packed away, so that those wearing a silver brooch and fancy outfit could not earn precedence over rags and a simple garnet pin. Upon arriving in Van Diemen's Land their belongings would be handed to the matron of the Female Factory in the presence of their owners to be kept until their release.

The money they had brought with them in gold, silver, copper and soft was ordered to be handed to the surgeon-superintendent, who entered the amounts into his cash book and, upon arrival, lodged these funds with the authorities in Van Diemen's Land. They were to be returned to the owners at the completion of their sentences.

This inventory of cash was undertaken by Tiberias Potbottom and such became Mary's fear that she would never again see what rightfully belonged to her, that at the risk of the most severe punishment if she should be discovered, she elected to keep her small personal horde of gold coins. Fifteen gold sovereigns remained from Ikey's gift and this she kept in her 'prisoner's purse' along with Ikey's medallion.

The prisoner's purse, readily obtained for a few shillings in any English gaol, consisted of a small metal tube of brass with a fitted cap and rounded end. It was fashioned in much the same manner as the cigar-shaped container Ikey had caused to be made and which had carried his letter of credit, so comfortably worn by Marybelle Firkin when she had travelled from Birmingham to London. Only, the prisoner's purse of the kind Mary wore was much smaller and made to fit, without too much discomfort, in either of the 'treasure caves' that is to say, the rear or front orifice, convenient places to bury contraband on a female person.

On bloody pusover days Mary would transfer the brass container to within the rear cave, which although uncomfortable was safe from Potbottom's supervision, and the probing fingers of the convict matron who would examine that other part of her anatomy and report it free of infection to the surgeon's assistant. He hovered behind her with quill and ledger in the hope that he might be able to record a finding of pus to transform into profit.

From the time the prisoners began to arrive the Ladies' Committee commenced to visit the ship. Mary, suspicious by nature of charity, was at first wary of these high-minded women, but she soon grew to respect them. Though pious in their ways they earnestly sought to alleviate the discomfort of the voyage and could, on occasion, become quite cantankerous if they found a facility in the prison which did not adhere to the prescribed regulations.

Potbottom did his unctuous best to earn their approval, dancing attendance like some small simian creature trained especially for the task of serving, assuring them with much dry-soaping of hands and nodding of head and frequent obsequious expression of his utmost co-operation. He insisted that any complaint they might make would be his personal pleasure to attend to in the time it took to snap his greedy fingers.

Nevertheless the formidable Mrs Fry and her Ladies' Committee were not easily deceived and they soon earned the approbation of all but the hardest and most recalcitrant female convicts. Though the world of the two classes of women was divided by a chasm too wide to leap, or even for one to imagine the life of the other, these committee women were not from the authorities, nor were they easily intimidated by them. Furthermore, they laboured trenchantly and with goodwill on behalf of the female convicts. They showed themselves as women who cared greatly for their unfortunate sisters. By notable contrast, with the exception of many of the surgeon-superintendents who often took the utmost care of their convicts (Joshua Smiles and some few others being the exception), the male administrators were, for the most part, totally indifferent to their welfare. In fact, most went to great pains to indicate that they cared not a rat's tail for the wellbeing of their charges but, instead, regarded every female prisoner as a whore transported to keep the men, both convict and free, sated.

Mary's misshapen hands did not allow for needlework but to her great delight, along with cloth and thread, the resourceful Quaker ladies had supplied a small library. While there were no novels, plays or other improper books, the single box contained, as well as religious works, travel, biographies and history books and poetry. This last gave Mary a new-found pleasure, and was to bring her considerable joy for the remainder of her life.

Most of the convicts on board adapted to the order and routine the Ladies' Committee established at the commencement of the voyage, and those within Mary's mess, though all of them prostitutes, encouraged by her, soon proved eager to take up needlework. They were frequently rewarded for their diligence by Mary with readings while they worked, but this was not true of Ann Gower's mess.

These were the women who were branded by the authorities within the surgeon-superintendent's report at the conclusion of each voyage with words such as, 'notoriously bad', 'disorderly', 'profligate wretches', 'quarrelsome', and for those with a flair for invective and a good, well-inked goose feather quill, 'the basest and most abominable wretch of a woman', or 'scheming, blasphemous vixen and prostitute' – this last description being appended to Mary's name by Tiberias Potbottom on the very first evening of her coming on board. When the ship arrived in Hobart, this single entry in the surgeon's report resulted in her being incarcerated in the Female Factory instead of being assigned as a servant to a settler. In truth, with the exception of theft and blasphemy, fighting and the urgent couplings which took place at night, most of the offences committed on board were minor breaches of discipline such as insolence and refusal to obey orders, howling and singing a hymn or prayer to the tune of a well-known bawdy and sentimental song.

In the week before the departure of the vessel the relatives of those convicts on board began to arrive to farewell their wives and daughters. Mary, having no family of her own, witnessed the piteous sight of parents parting from their daughters with no likelihood of ever seeing them in this life again. The deck of the Destiny II was washed with the tears of country folk who had seen their dear daughters leave home to find work as servants or some form of livelihood in the city only to end up, unbeknown to them, selling their bodies on the streets of London, Dublin, Glasgow or Liverpool or resorting to petty crime in order to stay alive. These were good, honest people, who, for the most part, worked at backbreaking labour to earn barely enough to put bread and broth upon the table. They brought what they could as gifts, though frequently this was no more than the tears they shed and the love they bestowed for the last time upon their unfortunate and wretched offspring.