Scarleteen

I (17F) started experimenting with masturbation when I was about 14. I read countless stories about it and my biology class helped me understand my own body. I tried to masturbate like I read in books with my finger on my clit, or humping a pillow, but I couldn't orgasm. I got no pleasure from penetration with my fingers, and it just added to the frustration.
It frustrated me so much that I stopped trying to, and would just masturbate until I got tired. Eventually when I was 16 I bought a vibrator and was able to cum for the first time. It was intense, but it was the only way I knew.

I now have a long distance boyfriend and we sext through writing messages or being on call while we role-playing him taking me or me using a strap on him.
I recently told him about how I don't get pleasure from penetration, and now he's feeling anxiety about it because what if he doesn't satisfy me? I've reassured him but now I'm trying to find some way of fixing this problem I have.

Hello PathLessTaken, welcome to the boards!

So, it sounds like you want to experience pleasure from penetration and orgasm without a vibrator — is that right?

We can absolutely explore ways to address these concerns, but I wouldn’t necessarily think of them as problems to be fixed. Often, it is better to work with your body as it is than to try to make it do something different. Penetration isn’t the only pleasurable part of sex, so even if that was off the table, there are so many other ways for you and your partner to feel satisfied together.

To start, I wonder if you've tried including clitoral stimulation during penetrative sex. The clitoris has more sensory nerve endings than the vagina, so it could make things more pleasurable. You can use a vibrator to provide this stimulation since you've already had good results with it, and you can try this on your own or with your partner.