A few years ago I was searching through xnxx with a phrase something along the lines of "mature older female teacher seduces younger male student". Specific, I know, but I remember having to narrow it down that much to stop getting 'older male fucks younger female' sorts of videos. This search ended up with me finding Carrie Moon starring in a 9 minute clip titled "The Tutor", where Carrie Moon's breasts distract the teen guy she's tutoring to the point where she offers to jerk him off and get it out of his system.

I think, after enjoying that clip, something caught my eye under related videos. IIRC, the thumbnail was a mature-looking woman sitting on a couch with a young looking guy. The scene of this video that's on the TOMP was something along the lines of our two characters looking through a photo album or a scrapbook on the aforementioned couch. One picture (not shown on screen) catches the guy's interest, and the woman gives an explanation, something along the lines of "that's my grandmother, she was a (showgirl?) and wore that outfit all the time". In typical porn fashion, this leads to them getting intimate (don't remember what kind of sex though).

Hopefully I'm not making this up, but I haven't found the clip after quite a bit of searching. Lemme know if this rings a bell for anyone!