I've reached a point where I really wanted to try actual cuckolding, so a few days ago I went ahead and told my fiancee about it when we were cuddling in bed. We've watched interracial porn a few times, so she was already loosely familiar with my interests.
From the posts I've seen on here and on reddit, I was worried that it was going to take a lot of convincing or that she would be completely disgusted with me, but she was surprisingly relaxed about the whole thing. She told me she felt excited about trying new things and she assured me that it's just harmless fun and that a lot of couples experiment with things like that nowadays and that it's nothing to feel ashamed over. I guess it really depends on the type of girl you are with, but I don't think they will always automatically be against the idea or only put up with it for the sake of her boyfriend or husband.
We haven't planned anything yet so far, but I will look into finding a male escort for her.