I have fucked older married women many times. They really appreciate the attention that you give them. They are so surprised when a younger guy wants to eat them out before fucking them.

Yes, 22 to be more exactly. She was a classmate and friend in university, I was 25 at the time.

We become friends with benefits, and damn, it was the best sex I had in my life.

I have not and don't think I've done 20 years younger either. Maybe 10 younger, 5 older? Generational differences squick me right out, I am somehow more appealing to guys younger than me (always been that way I don't know why) but at this point some of those guys look like kids to me.

I don't have problems with lubrication, but gamed it by starting out very juicy and also I use the estrogen cream to keep healthy down there, it really helps.

Yes, a few older DILFs and a few sigar daddies

When I was 25, I had a 6-month affair with a 50-year-old woman coworker who looked like she was 35. She was a receptionist at the moving company I worked at. She used to hang out at the bar with us, light flirting and touching from her, until we walked out and she grabbed me by my crotch. Next thing you know we're in my car sucking my cock all the way to my balls, until I came and she swallowed it all, something my (X)wife would never do. The next day she invited me to her house, (which was on my way home) and we fucked in almost every single room of the house. She absolutely loved anal, having her pussy eaten and fucked. The best part about it was she would make sure to suck my cock, and balls clean so when I got home and fucked my ex she had no clue. That went on for 6 months until my ex caught me fucking her on the hood of my car behind the bar.