I would assume if there was a love interest it would be esdeath as she most likely matches him the most. I also assume he won't prostitute his woman/lover right just the slaves he picks up otherwise that's a put off for sure
Def not, not a fan of that kinda thing, the prostitution ring is mainly a source of income and easiest way to display his control over people, he likes being in control, but nah to what you said