About 8 or 9 years ago, I answered a Craigslist ad from a couple--back when you could still do that. They were seeking a "Hung Stud to Fuck Hot Milf Wife." The husband was in his early 50s, but the wife was in her late 30s at the time. They'd been married for about eight years, and the husband had had cuckold fantasies the whole time. He was a fairly typical cuckold. He was rich, went to a big college, and he had a smaller than average dick.
Well, I traded pics with them for a few weeks, and then we cammed a few times. The wife looked really fucking hot in the pics and vids, and she was super flirty and super-sexual on cam, too. She was tall and had really nice, perky c-sized tits. Her ass was insanely cock-stiffening. I mean, she had the nicest, tightest bubble butt, and she was trimmed but not shaved.
After about a month of back-and-forth texting and camming, we eventually met up. I played around with them a few times. The wife was really fucking hot, and she loved it in every hole--she was really a performer, too, and she loved to humiliate her husband. She texted me on the side one night and asked if I would be willing to fuck her in front of a group of strangers. By that time, I had already fucked in front of crowds of 20 or so a few times, and I really loved it, so I said yes to her, and told her that I had some ideas of my own.
I knew this guy, an older guy, who owned a bar, and he and I had been friends for a while, and had even tag-teamed one of his old girlfriends a few times. I asked him if we could use his bar as a site for a nice hard public cuckolding. He was game. His idea was to close up on the early side one weeknight and invite a few select people along to watch.
The husband knew we were gonna fuck that night, but he had no idea what was really in store for him. We met at the bar for drinks, and he and the wife got pretty hammered. I had a couple of drinks and went out to smoke some weed.
I had already arranged most of what happened afterward with the wife. When I came back in, the bar was closed, and the husband was handcuffed to his chair. I went and stood beside her and ordered her to take off his pants--which was kind of hard because he was sitting down, but she managed it. The dude had on a cock cage and no underwear. There he sat in front of maybe 15-20 really drunk friends of the bar's owner.