Like an earlier poster, mine would have to involve going back in time so it can never happen.
I'd go back to the late 70's/early 80's and somehow arrange a match or instigate a battle between a woman named Tina who lived on my street and my friend's mom Nina.
Tina was kind of exotic looking with long straight black hair down to her ass. Wore a lot of makeup, big earrings, etc. At that time she was early 30's. Built very nice. Nina back then was in her early 40's. Shoulder length black hair. Busty 36D build. They were probably about the same weight but Tina had about 2-3 inches on Nina.
I'd maybe spread a rumor that one said something bad about the other and hope that it would result in a confrontation. I have little doubt that Tina would get the best of Nina.
What I would really want to do is arrange a match between the two. I would be the only spectator. It would be in an upscale hotel suite. Nina would be in white bra and panties; Tina in red bra and panties.
It would be a one sided match with Tina dominating and toying with Nina.
At the end Tina would take Nina's bra as a prize.
Then I would sit astride Nina. She'd bring her breasts together around my dick and I would tit fuck her until I exploded all over her breasts.
Yep, pretty sure that's never going to happen. Love thinking about it though!!!