It's wrong to judge, but A44, for someone to frequent the same lady so often and trying to keep a "tradition", it gives the impression that you are someone who craves the stability of having a steady partner. Surely it goes against the behaviour of a real "player", or even a serial punter for that matter.
I'm not making any judgement or saying anything is wrong with your behavior (believe me, I've done far worse than what you are doing... I'll probably burn in hell!!). This is just my observation, that's all.