Wouldn't. Looks too much like the bookkeeper I worked with at my high school job. Her boobs would occasionally liberate themselves and take a breather on her desk while she was reviewing my work. Even as a young guy who spent all day in an all male high school, I was just simply not interested in her speckled squid eyes.
Also I totally would because there is something about her I find attractive. Maybe it's because she's being really motherly and sweet about guys getting their nut off. I was always afraid of browsing weird shit and stumbling upon something I am into I never thought I would be. The internet is like a minefield
Indeed. It seems like she'd be tolerant of my eccentricities and concerned about my orgasm. Heck, the fact that she's clearly unembarrassed discussing this sort of thing is probably a recommendation in itself. Fewer beauty products might be a good idea, though.