Yeah use "Shemale" at your own risk... I know I'd probably think twice about going out with a guy who used that word too much.
It's from porn, and porn is all good, but would you honestly walk up to an attractive woman in her 40's and call her a MILF? Or drop that in casual conversation around her? "Hey guys this is my MILF date." "I'd like to introduce you to Mary, she's a MILF".
Probably the universal faux pas in dating a TG is to use the wrong pronouns. Even escorts who advertise as "shemales" will show you the door if you call her "he". I've heard stories of guys in Thailand who wouldn't stop calling their LBs by male pronouns. Not only were they treated very coldly by every LB they met for the rest of their vacation, they had a couple of LBs who were so offended that they harassed the guy every time they saw him on the street.
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