MILF

Kyle ordered an iced tea as he perused the menu. He looked up and saw a woman enter. He noticed it was a MILF actress. He had never slept with a woman older than forty, and thought having sex with an older, mature, and more experienced woman would be interesting if not outright fun.

1) It's Joely Richardson:

2) It's Lena Heady:

3) Connie Britton

4) It's Heather Graham

5) It's Louise Lombard

...