Well, on one hand, I have to admit that the sight of a well shaped set of gams in the air (and I definitely have that) topped by a pair of CFM 6" heels is definitely very sexy, as confirmed by a few gentlemen. So, there is definitely something very sexy about leaving the heels on LOL

On the other hand, for me at least, it takes a little away from the overall experience, because at least one portion of my brain needs to be every mindful that I am wearing potentially lethal weapons if I should get a little over enthusiastic. Worrying about squeezing a man's head off is enough (and sometimes I do), adding the potentially lethal element of heels is almost too much.

Ok, so I exaggerated mabye just a teensy bit for the sake of humor, but heels do actually present a bit of a challenge. I think they do look sexy myself, so if a gent asks, I'm happy to wear them.

I simply add the disclaimer that the operator is not responsible for any possible body injury that may occur during the experience

I saw a gal last summer who answered the door in thigh-high boots and a miniskirt. She looked hot but when we got down to business she didn't take the boots off...I went along with it, she said they made her feel sexy, but it felt a bit weird...
I prefer bare feet, in fact, I like it when the lady answers the door in her bare feet.
Porn producers seem to think that stripper shoes look sexy. I prefer the natural look on video as well, though a little pre-boink strutting around in the 7" heels is ok by me...

if you don't want her wearing shoes to bed.

It's easy for them to get tangled in sheets, and a twisted ankle isn't sexy for anyone.  I treat them like any other sexy accessory -- they're great sometimes, but only if they're not going to spoil the vibe and only if everyone likes them.