Re: my first post... please help
It's important for you to learn how to orgasm by yourself first. Then you can help your boyfriend. Spend some time alone exploring your body. Pay attention to what feels good. It may not be penetration - it could be gentle stroking of your clitoris, your labia, your nipples, some combination. Get a vibrator. Some women simply need the more intense, focused sensation of a vibrator on the clitoris to climax. Once you've had one orgasm, you'll know what it feels like and it will be easier after that.
The clitoris is a complex structure that goes deep inside the body. The part you can see is just the tip. Your boyfriend might have a hard time getting aroused and climaxing too if his penis was buried inside his body and he could only touch the head.
Your boyfriend's insecurities are not helping either of you! He needs to relax and not have so many expectations!