I've pretty much have done only masturbation for 3 or 4 years, until I became FWB with two wonderful guys. However, it's really difficult for them to make me cum... I keep on getting close, but never climax. It doesn't really matter for one guy, but the other loves, loves, loves cum. It takes a lot of work for me to orgasm from masturbation, so I know the problem isn't completely based on others. After becoming hard from whatever material I'm looking at, it takes a lot of energy to jerk off, to the point where I'm almost too tired to wank any more. I have to go really fast to accomplish the task. I can't do this more than once a day without my dick becoming sore. I have always used soft blankets to make it easier, but in the past year I have been doing it without the aid of anything so I can become used to ejaculating using only the sensation of skin. Any tips?
You seem to be over thinking it. Relaxation is key, don't wank to come, wank for pleasure, enjoy the feeling and focus on the feeling not the end result.