With your gf/wife, ask for it and see how she reacts. Most people are judgmental, sure you will get some that won't mind.
Asking for it from an SP is easy, you don't know her and don't care what she thinks of you.
I think this is a little more of a generational thing, when it comes to nerves of wives over the subject, along with the influences of ones cultural up bringing. We live in sexually charged country, along side others, where I think people are actually a lot more open about their sexual experiences, sharing stories among their peers & not to forget the almighty google which enables everyone access to all sorts of random knowledge within seconds.
You are also comparing the reaction of a civilian and one of a professional who’s mostly likely been asked for all sorts of “odd ball “ things, with strap on play being on the calmer side of the “ OMG !!!!!” scale.
While it’s our job to make our guests, who we don’t know, feel safe and comfortable enough to let us in on some of their secret desires, it’s your job to care about what we think of you. Nothing super analytical or over the top, but definitely to a certain degree if you’d like the opportunity to come back or be favourably mentioned in a Referal process through other ladies. “Caring “ too much about what others think including us professionals is what’s holding men back a lot of the time.
I don’t know how many regulars over the years there were who thought that they were “ far out there kinky “ because they wanted me to provide various types of strap on play, and they actually were woried that I would think differently of them. They also believed it to be an uncommon requests when its actually far more common that they know. Far far more common, and it doesn’t have to be the full strap on play but just ass play in general.
I’ve found that there are plenty of men who enjoy some kind of “play” and never mention it for whatever reason, and then all those who don’t even know what they are missing, until they do ....