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?
Iām 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. Iāve worked a fair bit on bends so Iām fine now with two tone bends on 10ās on the E string on fixed bridge guitars. But shiiitttt it took a while to get to that. In the beginning Iād resort to using a guitar with a trem because the bridge actually drops pressure a little as you bend. Itās not a massive help but itās noticeable for sure.
Apologies from bringing up this old thread. Iāve learned a few things since then and one of them is this higher action stuff also contributes to a better pre bend position for a better grip on the string.
But the main thing Iāve learned with my foray into SRV with high action and 13-58 strings had me deal with fatigue head-on.
Without going into every aspect of managing fatigue with all the fretting economies and rest management, Iāll stick to the bending of notes.
The main thing I learned is the push motion is inefficient, Iām now using a twist motion from my wrist while keeping the fretted note and hand stiff, lot more power in the wrist, this means your thumb may need to be placed accordingly to be the fulcrum.
One more thing, closer to the nut, I tend to yank the neck up and down as well along with the twising. Hope this helps somebody.
Action definitely makes a difference. Two identical guitars with the same string gauge but different actionā¦ the one with action that is too low, it will be a ridiculous struggle to bend vibrato on the higher strings, and the one with higher action will be a breeze in comparison. I guess it probably has something to do with helping to get the other strings a bit out of the way.
I play with really light strings for bending vibrato reasons, and also because my hands are prone to being cold, so the less tension I have to put into it, the better. Itās really easy to blow or irritate a tendon/joint when youāre cold.
Iām curious what super light gauge strings do for speed thoughā¦ I would think as long as theyāre not ridiculously floppy it shouldnāt matter too much