Before I decided to just stick with hobby dating until retiring into a life of spinsterhood I would sometimes date civies if I was taking a break from the hobby at that time. I would never mix worlds though...only one at a time. My problem came in that I felt morally obligated to tell guys I had been a hooker in the past. Basically as soon as I have told any guy that they respond more or less like this:
Everything about their behavior around me changes and I lose all relevance in their life outside of anything sexual. I'm not "me" anymore to them...I'm just a story of this hooker they dated once that hasn't made it to past tense yet. No such thing as being an ex hooker to these guys- you are degraded and impure and it's a matter of knowing things about human nature that you can't unknow... basically, they see you as damaged goods but that usually doesn't stop them from wanting to fuck you anyway and they may or may not string you along emotionally as necessary.
I don't intend to date outside of paid relationships ever again but if I did then I would NOT tell a guy that I was a hooker specifically but I would make it very clear that I was extremely promiscuous in the past and had a lot more partners than they would feel comfy knowing about. The fact that I was paid really isn't any of their business and they don't need to know the exact number of guys as long as I'm not bringing STDs into the relationship from past encounters they should just let the past be the past.
That's my take on it anyway.
Oh and I LOVE your song jasmine...it reminds me of the kinda poems they had on Def Poetry Jam.