When I was still in my teens I had a wonderful girlfriend named Diana that was as sex crazed as I was. We fucked like we’d invented sex and most days there are 5 or more fuck sessions. As I got to know her I learned her mother had similar appetites. She did not live with her after her folks divorced (mom got caught banging a neighbor) so I didn't see her mother much.
The first time I met her I was bringing the daughter home and her mom was meeting us at the father’s house. When I pulled up with Diana on my motorcycle her mom was sitting in her little Fiat convertible. When we pulled up she made a dramatic exit from the car and was wearing a tiny pair of shorts and a little tiny 70s style crop top (this was maybe 1983?). This was all set up to dazzle me and it did. She made sure to turn around and bend over for something in the car a couple times and both had a mischievous grin the entire time. The shorts were similar to a favorite pair of Diana’s and she later told me they conspired on what her mother would wear.
The next experience related to her was when we were house sitting for her mom. I didn’t see her this time but we did use some of her sex toys including my first use of handcuffs. So yes, I fucked Diana in her mother’s handcuffs and also used a big dildo and early magic wand style vibe in her- all her mother’s.
The final experience with the mother was a weekend the three of us spent at a mountain cabin. My fantasies did not happen but there was lots of sexual talk and flirting and my ass got a good squeeze at one point. It’s a shame they did not just go for it. I am sure they could see I was “up” for it.
So, I’ve had that fantasy ever since. I’ve experienced most of my fantasies so if this never happens it won’t be so bad...but you never know.