Hi, maybe I can help a little.
When string bending, there are several things you have to work on:
1. It's about hitting (or getting to) a note that is higher on the scale than the fretted position. So, first thing you have to do is listen and decide which note you are trying to reach (1/2 tone higher, 1 tone(= 2 frets) higher, or even higher). So first thing you could practice on is in hitting the note on the fret eg 1/2 tone higher (= 1 fret) and compare that pitch with the bend you are making. Do that in different positions on the neck and learn to hear when you hit the right bended note.
2. Learning to bend is a great way to develop rock and blues tones, but also to train your ear. Bending makes it also possible to play eg 1/4 tone higher... things you can't do on a piano!
3. Next thing: is it a bended note that comes down? bc that's also a possibility. This is more difficult, bc you have to start with the bended note (directly in the correct position) and then bring it down to the "normal" note on the same fret position.
4. If the note goes up or down during the bend : work on different speeds of bending. You can have a solo that goes quite fast, but achieve great tones by sometimes slowly climbing up in the bend (eg. SRV style).
5. Listen to the bend and try to apply vibrato. This may be difficult. Also try to use vibrato on different parts of the bended note (whole note, beginning, end (=sounds cool!),...)
6. A "guitartrick" : try bending a note slowly on the B string (eg. the G note= 8th fret) and let the tone climb slowly to A (a full note bend). But just before you reach the A, release the B string (don't let it ring) and play the A on the E string (= 5th fret) .... and you hear some SRV! Try this slowly, and you will have a great time.
Hope I helped you with this. Maybe this is info you already knew?