the heels stay ON. i can see him having a fetish over something like feet; one of those repressed men who accidentally starts over-sexualising something that's pretty normal, actually. i'm not personally into foot fetish so i cant add much but i can SEE IT. i SEE THE VISION.
OH MY GOD!!!!!!! OMG! let me tell u, i def agree!!! i feel like he's the type of person who accompanies you while you're buying shoes/heels and he'll be the one putting it on your feet. also i also imagine him being on his knees just worshipping your legs and heels, he'll actually kiss your heels if you asked him to. i feel like he'd be the type of man who would go crazy when he sees you wearing a short pencil skirt + stockings + heels. also i do think he'll enjoy thighs esp when you're wearing stockings, he's def into thigh fucking !!!!
thigh fucking gepard . . . oh, anon, you get me. especially if he's reasonably inexperienced and the first time you see his cock you go all over stuttering and spluttering at the size of it - thigh fucking is a good compromise so you can get used to it, right?! and thigh fucking over the top of stockings with your underwear dragged down, shoe dangling off one foot . . . sigh <3