Little update: I installed some new strings on one of my guitars: 9-42s Ernie Ball XT (or similar).
They stick to the fingers a bit more than my usual Elixirs, so that makes bends a little easier!
PS: I am also trying to always use 4 fingers for bends on the high E - and that seems to help as well.
Where is your thumb when you bend? Do you keep it flat on the back of the neck?
I’m pretty sure every time I bend I have my thumb pressing down on the side of the neck (where the side fret markers are)
I put a couple pics earlier but they got lost in the big thread 
Is it just me or it is pretty hard to bend the high E string? - #25 by tommo
Having a trem, especially a floating trem, makes bends heaps easier. I’ve worked a fair bit on bends so I’m fine now with two tone bends on 10’s on the E string on fixed bridge guitars. But shiiitttt it took a while to get to that. In the beginning I’d resort to using a guitar with a trem because the bridge actually drops pressure a little as you bend. It’s not a massive help but it’s noticeable for sure.