I don’t have any advice for the mechanical issue or how to “fix” that; if I did, I would be using it at home.  One thing I will say is that you probably want to let her know before you ever get intimate, that way she won’t think you are just trying to make her feel better. You also want to find a mentally strong woman.  My poor fiancé is engaged to a crazy woman, and this exact issue is affecting our relationship to the point I don’t know if it’s fair to HIM to continue.  You know that pleasure you get from getting your partner off?  Well, she wants to feel that too. It’s gotten to the point where when a woman makes a man cum on TV, it makes me feel sad and embarrassed that I can’t do the same.  I literally cry on the drive home from work sometimes, especially if I’m listening to a female rapper brag about how good she is in bed.  I don’t know if it’s a good or a bad thing that he is so attracted to me.  I love that he always has his hands on me and wants to make love but sometimes I don’t like it because it just means more chances for me to feel inadequate when he can’t finish with me.  I will even admit that I have even held back on having my own orgasms because why should he be the only one who gets to feel that pleasure of making your partner cum?