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Your search for transvestites returned 4 broadsides
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Bonnie Lasses' Answer
Verse 1 begins: 'Farewell to Glasgow, / Likewise to Lanarkshire, / And farewell my dearest parents, / For I'll ne'er see you mair'. This sheet was published by James Lindsay of 11 King Street, Glasgow. The woodcut at the top of the sheet depicts a small town with three women standing talking together in the street.
This account begins: 'FEMALE FOOT BOY! / An account of the Extraordinary Life and Adventures of Catherine Wilson, an interesting young woman, about twenty years of age, daughter of respectable parents, near Perth, who assumed man's apparel at the age of fourteen, and hired herself to a drover, when she came to Edinburgh, and got into a respectable gentleman's family as a foot boy'. This broadside was printed by R. Reynolds, 489 Lawnmarket, Edinburgh.
Life of Jean Murphy
This account begins: 'The HISTORY and Comical LIFE of Jean Murphy. Shewing the enterprising scenes she came through when commanding a party of Rebels in Ireland : how she travelled Scotland in man's apparel'.
Verse 1: 'In blythe and bonny Scotland, where the blue bells do grow, / There dwelt a pretty fair maid down in a valley low'. A woodcut has been included at the top of the sheet. It shows a vanquished man in a wooded glade, surrounded by threatening advisories.