Breast feeding / latching

Fion
FTM . I am breast feeding my son, but every time my nipple hurts, every time I can't get him to open his mouth wide or even he latch on with wide mouth, he will move around and back to the narrow latch.  I met with the lactation consultant a few times, when I am there, I did ok, as they show me how to push his back towards me instead of the head and my nipple feels better not as pinch.  however, once I get home , I can't do the same thing.  I am already using the nipple shield. Any tips? 
Also how long does you baby stay on you breast for each nursing session? I am always worry he is not having enough milk from me... He only latch on anywhere from 10 mins to 25 mins total.  even at appointment, they think he is not gaining his birth weight back fast enough.
How much breast milk a 3 weeks old suppose to have ? 
Thank you!