Same here, well not milfs, I am meeting my regular SB tonight. I have booked a country hotel for the night and we will meet have a drink go and fuck then we will come down for dinner.
Back to the room where we drink, fuck and piss around generally until we fall asleep.
I pick up the tab (obviously) and she just wants me to pay and order her some books on Amazon or whatever for her studies (these are not cheap)
It's a bit unorthodox our arrangement in as much as i don't give her an allowance or rarely cash but i help out in other ways.
When we are out i guess i look like her Dad 
but little do people know she has her We-Vibe and sometimes her butt plug in Of course i get her to order from the waiting staff, they just think she has Tourette syndrome 
I would never overnight with a Pro$$ie but i find with a SB its more relaxed and less transactional 
I have a similar arrangement with a SA girl. I’m in my 50’s and she is 22. I don’t pay per meet but help her with money as and when needed, mostly for studies. I have no idea how I have managed to secure this good value arrangement, or how it has lasted so long, but I don’t complain
When we go out to eat, she likes that we hold hands across the table. I always feel very proud, and love watching other people’s reactions. Many blokes give me a “you lucky bastard” half-smile, and many women a look of incredulity!
The funniest moment was when we checked into a hotel, and obv its a double booked for two people. The late middle age female receptionist looked at me, looked at the SB, looked at me again, looked down at her screen, looked at SB, looked at screen, looked at me and said, in a flustered manner - “you do realise you have booked a double room - there is just one bed”?
To which I replied, “yes, thank you”. She handed me the key card with a look. The look was accompanied by no words, yet it said so much!
