Have you orgasmed from masturbation? If not, this is the best way to get to know your body and learn how much pressure you like, what kind of pressure, etc.
Once you are able to achieve an orgasm then you can bring this new knowledge to your boyfriend. Mentally, you may be able to relax a little bit because you KNOW that you can orgasm. A lot of women have a hard time because they're so focused on trying to have an orgasm, and not focusing on the pleasure that they are receiving. Or they think that the guy wants you to hurry up, or you're self conscious about your body. The list goes on. Mentally we can do damage.
Try fantasizing as well when he's stimulating you. Try and think of a very sexy thing and that will take your mind off of the nagging worries.
Also, you may benefit from the use of a vibrator. Many women have had their first orgasms with them. And I'm talking about 50 year old women who never thought they could ever orgasm.
Good luck! You'll get over the hurdle with a little practice!
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