Which MILF would you want to spend a night with?
What would you do to her?
The one with the light blue scarf on the right (their left).
I'd wrap her from ankles to neck in saran wrap, gag her with duct tape and lick/smell her feet while she squirmed on a bed making mmmphing noises.
Oh, ass training! Start slowly. Just some light touching will make anyone with no training jump around.
Work your way up to finger or two. But take the hood off. It's nice to see her face the first time.
middle right or very left are the only right answers
I might make her suck the plug like a cock before introducing it to her ass - muffling her moans while slowly using a finger or two on her first while she's sweating in plastic