Telecom: I'm getting a clearer picture..... First of all, try to take your focus away from her orgasm right now. She is not going to be able to do that until she can really relax. She doesn't need the added pressure. also, I'm sure some women here would disagree with me but: I have had great sex for a vry long time without having orgasms. IT's probably more of an issue for you than her. AS for as her self esteem, this probably is a big problem. I can tell you that I am considered attractive by most men and I usually turn heads. But, when the clothes start coming off, I get self conscious!! Women in our society are made to believe that we are supposed to look perfect!! The models and actresses are georgous, they have cosmetic surgery and teams of make-up artist, hairdressers, and personal trainers keeping them in tip top shape. They are plastered all over the magazines, billboards, TV, , movie screns, etc. This is what we see all day and you guys too!!! Of course we dont' measure up and we are aware of that. Find something specific about her appearance that you really like and tell her about it. That wil be better than a blanket "you look great" or "you are pretty or sexy" or whatever. Find something about your body or appearance that is flawed and point it out to her. Laugh about it and make a joke about it. She sounds like she is pretty open to trying new things. mutual masturbation is a good first step. Try tackling her one day and having a romp on the floor while laughing and tickling. Having "fun" sex will take the pressure and seriousness out of it and help her to relax with you. I think you should jsut work on her feeling better about herself and relaxing before you worry about her learning to orgasm. That will come with time. You seem like a great guy and I know that everything will work out. Your patience and caring attiitude will prevail!! Good luck! Sexy....