ixing the two worlds is a rather risky thing IMO. You could always hire two duo providers to offer your role play scenario instead. If they're good, you won't know the difference.  

Just a thought. Good luck, there are lots of ladies to choose from in this duo realm in the city

sounds hot!

With a good rapport, cruising together can be exhilarating & most rewarding!  I have never done anything quite like this with a client, and I'm guessing that a second date would be too soon to feel comfortable trying something like this, but who knows, sometimes solid rapports develop quickly after meeting.

That said, I love picking up men and women in social settings and taking them home to have fun.  I do it quite a bit in my free time.  Although I can't suggest a place to pick up cougars in NYC so I hope you would have a suggestion.  

Maybe we will meet someday if I'm your type.