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Today I'm going to take you back to 1963 and tell you the story of Gerald Trenton, who was discussed in the February 7, 1963 issue of JET.
I'm going to use female pronouns since Gerald expressed the desire to transition. Unfortunately the JET article doesn't chronicle the femme name.
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So after 60 job rejections, young Gerald decided since she was 5 foot 9 inches tall, had no facial hair and weighed 125 pounds, she would try job hunting as a woman.
Trenton said at the time, "I'm a terrible looking boy. But as a woman, I'm not unattractive; nothing special, but not bad.
Her dressing for feminine success paid instant dividends along with her fair skinned complexion that employers mistook for being white.
She worked as a waitress in a San Francisco diner for almost two years without raising suspicions, then quit that job to become a popular female illusionist at a local nightclub. But because she would get depressed when she had to switch back to male attire, she quit that job.
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Trenton then drifted across the bay to Oakland and shared an apartment for two months with two cis women. Unfortunately they stole her dresses and left her almost denuded of feminine attire.
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It didn't take her long to garner the amorous attention of her male coworkers. She remarked about him to JET, "That he paid more attention to things other than work."
The now 22 year old was chased around her desk, pinched and felt up by her boss as well to the point where she quit her job.
Trenton's luck took another twist when she was hanging out with some gay friends. They we minding their own business and having a great time, but the homophobic owner called the po-po's, who arrested her for 'immoral dress'.
Translation: violating the anti-crossdressing ordinance on the books at that time.
Trenton said, "I suppose it will be even harder for me to find a job now."
She expressed her wish to permanently become a woman and visit a Los Angeles based surgeon to make that happen.
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One thing we don't know if Trenton got her SRS wish fulfilled as well.