Cross dressing spy who caused a headache for British masters

tags: World War II, gender, United Kingdom, Great Britain, cross-dressing, espionage



As one of Britain’s top spies in the Second World War, being arrested in Spain dressed as a woman caused a major headache for his political masters.

Lieutenant Colonel Dudley Clarke, a key figure in British intelligence in the Middle East, was detained in Madrid after being seen “in a main street dressed, down to a brassiere, as a woman”.

The spy was on his way to Egypt to pass on key information and the incident sparked a mad scramble in London to ensure he was released and sent on his way as quickly as possible.

Files released by the National Archives show that Lt Col Clarke – who was supposed to maintain a low profile, travelling under cover as a war correspondent for The Times – had stopped off in the Spanish capital on his way to north Africa in October 1941....



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