I have never experienced an orgasm and have tried to masturbate towards one [by touching my clitoris using varying degrees of pressure, penetrating myself with my finger and or the bullet] but been unsuccessful.  I usually end up frustrated and give up.  My boyfriend inquired as to whether I even knew what one feels like, because while engaging in oral sex he says that he felt me spasm.  He said he wouldn't call it the big O but that it was progress.  He even bought me a bullet that we tried. But even with the bullet I've not reached orgasm. 
 

My boyfriend has been extremely supportive but I feel like there is something wrong with me and so I've been avoiding the more intimate aspect of our relationship.  I want to work towards reaching orgasm but don't know what else to do.  Masturbation, Kegel exercises (150 a day), meditation, relaxation and sex toys don't seem to have the desired effect for me.  Can you offer advice or additional methods to try?

Let me start by saying that Kegel exercises are not for helping a woman climax. Your clitoris, as you seem to know, is the seat of a woman’s orgasmic response and having strong vaginal muscles does not come into play with that. It’s good to do them because they can make intercourse more pleasurable, but they won’t help you with your particular problem, and I also think 150 may be a bit more than you need to do in general.

Because your boyfriend said he may have felt you having an orgasm and you didn’t, you may be suffering from what is called missed orgasms. Your body is having the physical response but it is not registering in your brain. Do you get any feelings of satisfaction? If your body is telling you that you’re no longer aroused but you didn’t “feel “ the orgasm then you are having missed orgasms. If that is what is happening, you should see a sex therapist. You can get help, but it is better to have professional guidance.

Finally, are you under any medical treatment, especially for depression? Certain drugs can have side effects that can cause someone to become anorgasmic (unable to have an orgasm.) If this might be the problem, then you should first consult with your doctor.