My wife passed away about two years ago and for about the last two months one of my step sisters has been making sure I am doing okay as she puts it. She did not graduate high school, ended up getting married when she was seventeen because they were pregnant, divorced in her thirties and has been working service jobs ever since and barely making it.
She has made it pretty clear several times that she would love to take care of me in all ways if I want which I find surprising because when we were growing up she would call me a creep if she thought I was checking her out. I have thought about starting something with her and slip my cock into her ass one evening on accident, if you know what I mean.