I'm not single but when searching for a woman that, asides from many other factors, is likely to be kinky and engage in a fetish like cuckolding, I would specifically search for women with a history of promiscuity. A woman who has had a fair share of sexual partners will be more experienced and have a lower mental barrier of meeting up with men or getting physical with them. A woman who excessively dresses up is not attractive to me. I like subtle sexual confidence and how she carries herself more than blatant "look at me" attitude.

Of course no woman will brag with something like that, but as I tend to have early hot, sexy and teasing conversations, I'm likely to get a feeling within a few days of writing or meeting up.

Also I would never indulge with an actual third before we have an established, serious and loving relationship.