Would I Hit It?
Trannyphobia induces a lot of anxiety related to PTSD (post tranny stress disorder), and shares much in common with fear of going to the dentist.
So, let's see.
First, I'd ask:

If so, my anxiety is lessened and, consequently, yes, I would hit it.
If it is not safe, my anxiety is heightened, so, hold on, give me a second:

OK, I'm ready. Yes, I would hit it.