Over at Crossdream Life gulliver.arkham has published a comprehensive overview over the times Sherlock Holmes has crossdressed as a woman:
Along with being the working definition of THE master detective, one of the things you soon learn on reading the original stories about Sherlock Holmes written by Sir Arthur Conan Doyle about Sherlock Holmes, hereafter known as “The Canon,” is that he was also a master of disguise. Appearing in disguise in 10 stories in The Canon, unless I miscounted, he is so good at the craft that not even Watson is able to tell who he was when playing at being someone else.
There are also crossdressing stories outside the canon, i.e. in stories not written by Conan Doyle.
The discussion also reveals that there has been a female Watson on TV (Elementary) and even a Japanese female Sherlock Holmes (Miss Sherlock).
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