"Among the colourful characters employed by MI6 was Lt Col Dudley Clarke who was arrested in a street in Madrid “dressed down to a brassiere as a woman” according to one report.
Clarke had been running a GCHQ deception operation in Cairo using the cover of a newspaper reporter and had traveled to Madrid to meet Hamilton Stokes, the head of the MI6 station there.
After leaving Stokes on October 17 1941, he was arrested by the Spanish police dressed, for no reason ever explained, in women’s clothing.
He at first told them he was a novelist studying the reactions of men to women in the streets and then that he “was taking the feminine garments to a lady in Gibraltar and thought that he would try them on for a prank.”
“This,” reported the British Embassy in Madrid to London, “hardly squares with the fact that the garments and shoes fitted him.”
The police were inclined to believe that Clarke was a “homosexualist” Stokes reported, but the German secret police, the Gestapo, alleged he was a spy.
After four days in custody he was eventually released and returned to Cairo where he “went on to have a brilliant career in deception,” according to the new authorised history of the Secret Intelligence Service."
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