Squirting lol...

Okay so I apologize for my lack of knowledge. I'm 17 and I have masturbated plenty of times. I have a boyfriend whom I have had sex with plenty of times as well. When I masturbate, I can never finish. I honestly don't even know if I have ever finished because I honestly feel like I could just keep going. But I know that my boyfriend will always finish before I do. So I guess I have 2 questions... 1. What does it feel like to finish and 2. Should my boyfriend and I foreplay (fingering, eating out, etc) for awhile before having sex so I'm closer to finishing and we finish at the same time.