My apologies to the late Helen Gurley Brown, the long-time editor of Cosmo and the author of Sex and the Single Girl, but my title seems appropriate because sex can be especially tricky ground to negotiate when you start dating pre-op or non-op ladyboys.
Alright, sex can be a minefield when you start dating a cisgender woman, too. But there are special things a man has to take into account when he and his new TS girlfriend are ready to be intimate. And in case you’re wondering, almost none of this applies if she is post-op.
Love what your ladyboy girlfriend have or hate It
Perhaps the biggest potential landmine is how she feels about her genitals. A relatively small number of transsexual women hate their penis. They don’t want it touched or fondled, and definitely do not want you to perform oral sex. Early on, a man who is smart and caring will gently ask her attitude about it. The way I usually raise the subject is softly but directly: “So it seems like we’re heading towards becoming a couple but before I accidentally do something in bed that you don’t like, how do you feel about me touching your penis?” Depending on the woman, sometimes I use a slang word. The question often provokes a laugh or smile, sometimes an embarrassed giggle. Only a very few women have said “Leave it alone.” But over the years, most told me in no uncertain terms something like, “I love having orgasms and if you don’t use your hands and mouth on me, we’re not going to be a couple for very long!”
