Recently my boyfriend has seemed very upset over the fact he can’t make me cum when we have sex. I have never been one to fake an orgasm because I feel like if I ever want to try something so I finally can, it would be hard to have the conversation with him without bringing up the fact I hadn’t actually done it before. There is nothing wrong with the way he is doing things and frankly, I’m not even worried about finishing because I enjoy the whole experience.

On the other hand, I can easily make myself cum when masturbating on my own. He knows that and thinks there is something wrong with him physically. I try to reassure him it doesn’t bother me and I’m not sure what to change about things but he still seems to be very effected by it (like it damages his self esteem).

Have any of you ladies had an experience like this? If so, how do you handle it? Are you able to orgasm now? How do I raise his self esteem without faking it?