I would love to be able to masterbate alone and actually get some satisfaction. But I've NEVER gotten anything out of playing with myself. Now if I'm being watched (especially if he is jerking off to it) or even if it's phone sex, as long as someone is getting pleasure from it to, now that's a different story. How can I get myself off without needing help?
I gotta admit, I find being watched a real turn on. As for getting off when you're on your own, you could imagine that someone is watching you through the door lock and is getting off, or stand in plain view in your front window and see if you can catch a neighbours eye. If all else fails how about finding a Skype buddy.
I'm curious about the psychology behind this one, I could guess that it gets you off knowing that someone else is feeling pleasure, which is common. Though I don't know how common it is for masturbation to be unsuccessful without something else going on at the same time. Sadly, I can't think of much good advice, except what the poster above me suggested. Have you tried porn, just to get out of your own head even? I know that I struggle on my own unless I'm watching/imagining something out of my own specific fantasies.
Even as a teen I was never successful at satisfying myself. It has just never really been a problem, I've just never been a masterbater. Now that I'm getting out of a very long unhappy marriage I am realizing how sexually deprived I've been and I'm horny ALL the time. And unfortunately I don't get to see my boyfriend every day I'd love to be able to take care of my own needs once in a while.
Sounds like you need to relax into getting used to feeling attractive, desired and sexually confident. My wife fibs it difficult to cum sometimes if she's not in a particular mood. So, just chill out about it and think about how horny you make your boyfriend when you masturbate in front of him. Oh, most of all Have Fun!