Alright brother, I'll let the Chicago gents share recommendations - but I will opine on the common pitfalls to avoid:
1) getting scammed by a bogus ad. Anytime I see a hot ladyboy ad in the USA, I'm skeptical. They are the rarest of unicorns here. The higher concentrations are in California, but even there you need the bullshit detectors turned on.
The link you shared actually belongs to a Filipina TS in Manila. I figured this out by reverse searching her images in the Chicago ad. You may have been actually greeted by an Asian person, but chances are higher it would have been a black man in a wig, high on drugs, ready to steal your money and pride.
2) bottoming - having a good clean BM just before the session isn't enough. make sure you enema douche thoroughly. I just keep filling the bottle with water and rinse maybe 8-10 times. Also, bring your own condoms, lube, and anal de-sensitize product with you.
Other thoughts: If you can afford it, go to the source. I've traveled to San Diego/OC area just to fuck Asian TS girls. There's plenty of choices and what's not to love about a weekend in California in the middle of a bitter Chicago winter. Filipina girls are more likely to be verse, horny, freaks.
And when you need a vacation in your mind.. take a look at the Casual Encounters t4m ads for Bangkok, Manila and Hong Kong on the site that rhymes with Eggs Fist.
-- Modified on 12/22/2016 4:27:21 PM