Mistress Ayn,
Points 1, 2, 3, 8 and 9 were usually done in the mid-20th Century by a straight married male who was married to a gorgeous woman. Or were rich and had a gorgeous mistress (lower case, not "Mistress" or Domina) who was being "supported" financially by him.

In other words, the older man was a gentleman, but he was in the "deep end of the pool." Such men were sugar daddies, there to pay at Lord & Taylor, Saks Fifth Avenue, Berdorf Goodman in Manhattan when they were classy joints to shop.

I kinda know all this based on stories I heard from a couple of Aunts of mine who had college friends from the '40s and '50s who had businessmen who admired their friends and took them... shopping. wink