Category Archives: Crossdressing

And who would you like to date today?

(Disclaimer for those who need it: There is zero evidence that Gertrude Olmstead was bisexual, lesbian, or any other sexual preference except straight, so despite comments here, her honour should be treated accordingly. Indeed she was married happily for 42 years, until her husband passed away. However, she seems to have had more than a few shots taken, gender cross style, so who knows?)

As someone who (all too often) went out on dates as a man, for obvious reasons at the time, I do think its a bit of a shame that I’ve never got to do a proper date as a woman. Clearly I’ve done group meals as a woman, and indeed had a few dinners alone with Eric, but nothing in a romantic sense, though some of the restaurants might have thought otherwise. No, I’ve never done an actual date with a woman, as a woman, now that might be fun too!

But how about the ultimate in amusement, a date, me dressed utterly feminine, and a woman, dressed in a more male style? Therefore, when I saw these two pictures of said lady, Gertrude Olmstead, on one of the vintage Facebook groups recently, it did amuse me that I fancied her in both styles

Twist my arm, an all girl date would be heaven. But seriously, her dressed like that, as a man, oh goodness, I could easily swoon in his arms, and let ‘him’ have ‘his’ wicked way with me! As I say, checking her out on Google images, this is far from her only ‘boyish’ image, but its wrong for me to suggest anything more than for film roles, or promotion shots?

But fine (she died in 1975, aged 77), post my SRS surgery, her with a strap on, I could just be in heaven! Is it silly to want to have sex with a woman dressed as a man that way? Oh, and I’ve found an earlier shot of Gertrude, where I could very happily swap places with her!

Gertrude 3

I know, you could soon get your arms out of there, but I doubt I’d want to, given its Lon Chaney threatening to do something evil to her, back in 1925!

So yes, RIP Gertrude Olmstead (1897-1975), and please forgive me this little piece of wishful thinking. But yes, take it from me, you have the style to look gorgeous as both a woman, and a man!

The video, another woman that seemingly I could fancy as a woman, and with the right, minimal makeover, as a man, Laura Branigan. Apt title, lol!

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