Ok, what I'm about to tell you is a judgment call. By reading some of your posts, your judgment isn't good in every situation. But anyways, you just gotta whip it out breh. Whip it out and see what she does with it, only two things can happen, (1) she ain't fukkin with it and you take an L or (2) she'll get down with it. For some it's a last resort, but honestly I do it just to see where a shawty head at.
In summation, I think you're overthinking this whole situation. Just go for it, you want some p*ssy go get it and stop thinking and putting up these barriers in your brain