As the boyfriend/husband of a lady who likes to squirt, all I can say is practice makes perfect. Guiding someone with real-time suggestions is certainly an option - but sometimes that can be a bit distracting.
Discuss what works best for you before hand - and suggest that he learn to read your arousal clues. I can read my wife like a book, I know what's working and what's not by her physical reactions. Level of lubrication, breathing, sounds, elongation of her vagina. and when I'm not getting it - she will gently suggest that I 'move on' or try something specific.
It's like a symphony - with you as the conductor and instrument.
If your guy is at all interested in your pleasure - he will welcome the suggestions - if not - find someone who is more interested in you than himself!
I recently taught myself to squirt and can do so very well solo!!! But How can I teach my boyfriend to make me squirt????
well, hopefully you guys are open enough for you to just show him. it will be very hot. lay back like you would when doing it by yourself but describe what you are doing as you do it. any male who wants to call himself a man should be an incredibly good student.