After i do the first barrel the yoyo is either toucking my finger that has the string or it just flies of???
Keeping it on the strings just takes practice. As for the other thing…Start the barrel rolls with the yoyo farther from your hand.
This question pops up a lot, here are some tips. Move from your elbow, and just keep you fingers in line with the yoyo, thinking about doing the next swing forward helps me keep them in align with the yo-yo.