Two years later, after the Nazi takeover, he applied for an extension of the Transvestitenschein. Winkelmann pleaded that the discrepancy between the name on his papers and his appearance prevented him from getting a job, and that he could not wear female clothing because he was always taken to be a man. He stressed that he was not a lesbian. Three officials found his case to be plausible in that he looked like and passed as a man. They ordered the police to keep an eye on him.
In April 1936 the case was passed to the Geheime Staatspolizei (Gestapo), who requested a report from Herrn Professor Dr. Müller-Heß of the Berlin Institute for Forensic Medicine (Psychiatric division). His report is no longer in the archives.
In February 1940, the application was reprocessed. However it was announced that Winkelmann was a woman and must dress accordingly. A change of first name from Gertrud to Gerd would not be allowed. Winkelmann attempted to live as a woman, but met great humiliation.
- Landesarchiv Berlin, A. Pr. Br. Rep. 30. Berlin C Tit. 198a 5. Allgemein, Nr.79.
- Rainer Herrn. Schnittmuster des Geschlechts. Transvestismus und Transsexualität in der frühen Sexualwissenschaft. Giessen, 2005: 163-4.
- Jane Caplan. “The Administration of Gender Identity in Nazi Germany“. History Workshop Journal, 72, Autumn 2011: 173.